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Filemon
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[*] posted on 4-8-2006 at 12:18
Amphetamine from Cinnamaldehyde


I was thinking to make amphetamine from Cinnamaldehyde:

1. - Cinnamaldehyde + HCl--> 3-Phenyl-2-chloropropanal. But may it self-condenser?

2. - 3-Phenyl-2-chloropropanal + ammonia--> 3-Phenyl-2-amino-propanal

3. - reduction of the ketone.
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[*] posted on 4-8-2006 at 12:28


You will make a mess

Quote:
1. - Cinnamaldehyde + HCl--> 3-Phenyl-2-chloropropanal. But may it self-condenser?


it will polymerize.

Your second proposed reaction would not work either; at the very least your amino-aldehyde would self-condense.

Your third suggestion, "reduction of the ketone": propanal is an aldehyde.

Cinnamaldehyde can best be cleaved w base to yield benzaldehyde.

From there you can go w acidic MEK aldol condensation, followed by Baeyer-Villager oxidation and subsequent hydrolysis to obtain P2P.

Details you can find here and on other websites more dedicated to the subject.

Be aware that in most countries it is a felony to produce and/or possess amphetamine without a license.





[Edited on 4-8-2006 by Vitus_Verdegast]




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[*] posted on 4-8-2006 at 13:40


It is a pity that one has to cleave the cinnamaldehyde just to go through serious hassles to attach this carbon again.

Isn´t there another way? Through the epoxide maybe? If I am not mistaken then there are two different epoxides possible depending on the conditions of the epoxidation, base or acid catalysed.

Just musings, I had no closer look into this I admit.

Addon:
Cinnamaldehyde -> cinnamic alcohol -> reduction followed by bromination -> amine

Step 1 by yeast almost quantitative IIRC
Step 2 by HI in excellent yields
Step 3 oh now I forgot what we get in 1, either HBr or Br, yields depend
Step 4 methylamine, good yields

or

Step 1+2 Clemmensen or catalytic hydrogenation

Something wrong with this? Sorry I am tired....

/ORG

[Edited on 4-8-2006 by Organikum]
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[*] posted on 4-8-2006 at 14:28


I would first reduce the Cinnamaldehyde to Phenyl-1-propen-3-ol with NaAlH4/NaBH4. Then I would chlorinate the alkohole with thionyl chloride to form Phenyl-1-propen-3-chloride. Now form the grignard with Mg to get Phenyl-1-propen-3-magnesium chloride(Ph-CH=CH-CH2-Mg-Cl). Now add an acid like HCl or whatever, this will protonate your negative charged organic rest. I hope the double bond doesn't konjugate, forming Phenyl-2-propen (Ph-CH2-CH=CH2) but since a primary carboanion is more stable, this should be the minor product. Now you could electrophilic add HI, HBr or maybe HCl to the double bond, yielding Phenyl-2-halopropan (Ph-CH2-CH(X)-CH3) by the majority (makovnikow). The rest is clear I think, hope this works. Maybe you could reduce the Phenyl-1-propen-3-ol also by nascent hydrogen, but then I can't guarante the existence of the double bond afterwards.
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[*] posted on 4-8-2006 at 15:05


I think I have a better idea.... :D

I had a look at the possibilities to reduce both the double bond and the aldehyde in one step, obtaining hydrocinnamylalcohol.

Of course sodium aluminium hydride in THF does this job quantitatively in 5 minutes but we are looking for some more OTC solutions. Nevertheless some more or less promising references were found:

using lithium amalgam in EtOH/AcOH:
Yakugaku Zasshi 74 (1954) 1037; Chem.Abstr. (1955) 11593.

using fermenting yeast (nod to Organikum ;) ):
Justus Liebigs Ann. Chem. 529 (1937) 87, 100.
Justus Liebigs Ann. Chem. 513 (1934) 266,276
Justus Liebigs Ann. Chem. 522 (1936) 2,10.

using NiAl alloy in aqueous ethanolic NaOH at 90°C:
J. Org. Chem. 7 (1942) 587, 589.

using palladium in AcOH:
J. Am. Chem. Soc. 63 (1941) 3268.

using CuCl2.2H2O and Mg in H2O/THF (70% yield):
Tetrahedron Lett. 36, 39 (1995) 7119-7122.

and this one looks especially promising to me:

using electrolytic reduction in neutral solution at a lead cathode:
J. Chem. Soc. 101 (1912) 1017
J. Chem. Soc. 101 (1912) 1550.
------------------------------------------------------------------------------

Second step, once hydrocinnamyl alcohol is obtained, it can be passed over Kieselguhr at 400-500°C in a tube furnace, to obtain propenylbenzene:

C. R. Hebd. Seances Acad. Sci. 188 (1929) 638
The article, kindly provided by solo:
http://rapidshare.de/files/25876073/allybenzene_article___fr...

A quick translation of the article:

1. When allylbenzene vapours are passed through a column of infusorial earth heated at 400-500°C isomerisation to propenylbenzene occurs. Until the same conditions estragole and safrole are isomerised into anethole and isosafrole respectively.

2. At room temperature dehydration of 3-phenyl-1-propanol yields allylbenzene as the main product. For example, treatment of allylbenzene with SOCl2 yields chiefly allylbenzene and a small amount of propenylbenzene.
ref: Compt. Rend. 186 (1928) p. 1301, 1626, 1848

3. At elevated temperatures next to dehydration isomeration also occurs. When 3-phenyl-1-propanol vapours are passed over infusorial earth at 400-500°C propenylbenzene was the chief product, accompagnied with a small amount of allylbenzene.


From propenylbenzene, of course, standard route to the end product peracid oxidation etc...


Hydrocinnamyl alcohol is also available cheaply from the fragnance industry BTW. It is commonly used and not watched as far as I know.




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[*] posted on 5-8-2006 at 00:18


Quote:
1. - Cinnamaldehyde + HCl--> 3-Phenyl-2-chloropropanal. But may it self-condenser?

Of course you can't do a Michael addition on such an aldehyde due to reasons already stated. But in case aldehyde polymerisation would not be a problem one would get the 1,4-addition product, hence 3-chloro-3-phenylpropanal.
Quote:
Now you could electrophilic add HI, HBr or maybe HCl to the double bond, yielding Phenyl-2-halopropan (Ph-CH2-CH(X)-CH3) by the majority (makovnikow).

According to those rules (the nucleophile adds on the position where the most stable carbocation can form) you would obviously get 1-halo-1-phenylpropane by hydrohalogenating 1-phenylpropene.

I would say the reduction to cynamyl alcohol (or its aquisition given that it's pretty cheap), substitution with conc. HCl to yield cynamyl chloride, reduction with Zn/AcOH to yield 1-phenylpropene from which the route proceeds by well known reactions.




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[*] posted on 5-8-2006 at 10:51


Quote:
Originally posted by Vitus_Verdegast


Be aware that in most countries it is a felony to produce and/or possess amphetamine without a license.





[Edited on 4-8-2006 by Vitus_Verdegast]


Of course, they allow me microsynthesis but it should be immediately destroyed.
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[*] posted on 5-8-2006 at 11:16


I have in mind to use the Wolff-Kisher Reduction:

ph-CH=CH-CH=O + NH2-NH2 => PH-CH=CH-CH=N-NH2

PH-CH=CH-CH=N-NH2 + NaOH + head => ph-CH=CH-CH3
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[*] posted on 5-8-2006 at 12:13


You got any reference for that?

I highly doubt that is possible. In your fiirst post you seam to have been aware that cynamaldehyde is a Michael acceptor. Thus the nucleophiles can react with the double bond as well. In the conditions for the Wolf-Kishner reduction the hydrazide get on and off the carbonyl and thus adds to the double bond as well. I doubt that the reduction would go smooth.

[Edited on 5-8-2006 by Nicodem]




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[*] posted on 5-8-2006 at 13:10


here => http://www.chem.harvard.edu/groups/myers/handouts/1_Reductio...

pg.7

http://en.wikipedia.org/wiki/Wolff-Kishner_reduction

[Edited on 5-8-2006 by Filemon]
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[*] posted on 5-8-2006 at 15:47


Filemon, those links as provided do not prove your point. However, yield of propenylbenzene by the reduction of cinnamic aldehyde is 70% using Huang-Minlon variant of Wolff-Kishner:

http://rapidshare.de/files/28334409/huang.pdf.html

I meen you can't go from that aldehyde for the sake of going from there, even if it involves hydrazine reduction, hinz even suggests Grignard. If this starting material is to be used then I like Nicodems idea of making alcohol, then chloride, then OTC reduction. But to get to propenylbenzene you could go from propiophenone (cheap, IMO probably the best single precursor if you're interested in simple stimulants [including phenmetrazine, which at least Swedish speedfreaks prefer over methamphetamine according to Wikipedia, and one such person did report it better than amph on bluelight]
and have no regard for the law), reduce and dehydrate with tosic or sulfuric. Hell, there are other smoother ways of doing this, but amphetamine dosen't interest me, so you find out..



[Edited on 6-8-2006 by Sandmeyer]




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[*] posted on 5-8-2006 at 16:09


Whoops this post wasnt really needed, i didnt read sandmeyer's post correctly i though he was sayin it wouldnt work. But here's the post from the hive who discussed this method a while ago.

moo
(Hive Addict)
07-29-04 22:56
No 522534
Propenylbenzene from cinnamaldehyde
(Rated as: excellent)

There are two references discussing the Wolff-Kishner reduction of cinnamaldehyde to propenylbenzene.


--------------------------------------------------------------------------------


Reduction of Steroid Ketones and other Carbonyl Compounds by Modified Wolff--Kishner Method
Huang-Minlon
J. Am. Chem. Soc. 71, 3302 (1949)



General procedure

The reduction has been carried out by procedures similar to those described in previous papers1,2. Thus a mixture of the starting material, diethylene or triethylene glycol (Note 1), alkali hydroxide and 85% hydrazine hydrate (Notes 2 and 3) was refluxed for about half an hour and the condenser was then removed to allow the aqueous liquor to evaporate and the temperature of the reaction mixture to rise to about 200°. In cases where either the starting material or the reduced product is volatile a takeoff adapter was used instead of removing the condenser to evaporate aqueous liquor. After refluxing at this temperature for about two hours the reaction mixture was cooled, diluted with water (Note 4) and the separated reaction product was filtered or extracted with ether (Note 5).

NOTE 1. The amount of diethylene glycol or triethylene glycol used can be varied according to the solubility of the carbonyl compound or its hydrazone formed during the reaction so that a clear or nearly clear reaction mixture is obtained during the heating period. Sometimes it is advisable to dissolve the carbonyl compound in alcohol before addition of glycol and other reagents, e.g., in the case of cholestanone and cholestenone.
NOTE 2. The amount of alkali hydroxide used is about 10% to the volume of the glycol used and the amount of 85% hydrazine hydrate used is always in excess (3 moles or more).
NOTE 3. In reduction of alkali sensitive compounds such as aldehydes, ±,²-unsaturated ketones and those carbonyl compounds in which the carbonyl group is adjacent to an asymmetric center it is advisable to reflux the glycol solution of starting material with hydrazine hydrate for about half an hour and then add a concentrated aqueous solution of alkali hydroxide slowly as described previously.
NOTE 4. If the reduced product is acidic, it is obtained by acidifying the cooled reaction mixture with dilute hydrochloric acid.
NOTE 5. In cases where the starting material contains methoxy group the crude reduced product was remethylated with dimethyl sulfate.
NOTE 6. Most of the technical steroid ketones were recrystallized before reduction, since otherwise the yield is sometimes unsatisfactory. The yields of reduced products given in Table I are on the basis of pure products for which the melting points are given.
NOTE 7. In cases where the carbonyl compound is unstable and difficult to purify such as a-naphthaldehyde the hydrazone or semicarbazone can be taken as starting material for reduction.

(I took the liberty to omit all the steroid ketones from the table and leave the ones bees might be more interested in)

Table 1.
Compound Product B. p. °C. Yield,
% n25D
Vanillin 3,4-Dimethoxy-1-methylbenzenea 133-135 (50 mm.) 77.3 1.5257
Veratraldehyde 3,4-Dimethoxy-1-methylbenzene 122-124 (27 mm.) 81 1.5259
Cinnamic aldehyde Propenylbenzene 176-178 (755 mm.) 70 1.5464
aOn methylation of the crude reduced product with dimethyl sulfate.

1 Huang-Minlon, J. Am. Chem. Soc. 68, 2487 (1946)
2 Huang-Minlon, J. Am. Chem. Soc. 70, 2802 (1948)


--------------------------------------------------------------------------------


The other ref is Helv. Chim. Acta 35, 780 (1949) where the hydrazone of cinnamaldehyde is first formed separately and then decomposed with alcoholic alkali by heating in a pressure tube.



[Edited on 6-8-2006 by ergoamide]

[Edited on 6-8-2006 by ergoamide]
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[*] posted on 6-8-2006 at 07:49


Quote:

Hell, there are other smoother ways of doing this
Well Herr Sandmeyer thats called teasing. What about a hint?

And wouldn´t acetophenone or mandelic acid be the starting materials of choice for phenmetrazine?

;)

/ORG

[Edited on 6-8-2006 by Organikum]




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[*] posted on 6-8-2006 at 11:31


Quote:
Originally posted by Organikum
Cinnamaldehyde -> cinnamic alcohol -> reduction followed by bromination -> amine
[...]
Step 2 by HI in excellent yields

Really? Would that work for phenylalanine or tryptophan?

Quote:
Originally posted by Sandmeyer
including phenmetrazine

Interesting compound. What about the aminoethanol derivate (2-phenylmorpholine), is it pharmacologically active?
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[*] posted on 6-8-2006 at 11:40


Quote:

And wouldn´t acetophenone or mandelic acid be the starting materials of choice for phenmetrazine?
;)


A quick scifinder litt search revealed that the existing methods to that compound are not too good IMO, if I was to make it from propiophenone I'd take propiophenone alpha brominate it, swap the bromine with ethanolamine, reduce the keto function with NaBH4 and treat the diol with HCl to construct the morpholino moity. But since I will never brake the law it's up to someone with the propper license to test the route in practice.

[Edited on 6-8-2006 by Sandmeyer]

[Edited on 6-8-2006 by Sandmeyer]
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[*] posted on 6-8-2006 at 11:41


Quote:
Originally posted by turd
Quote:
Originally posted by Organikum
Cinnamaldehyde -> cinnamic alcohol -> reduction followed by bromination -> amine
[...]
Step 2 by HI in excellent yields

Really? Would that work for phenylalanine or tryptophan?
Huh? Thats both aminoacids and cinnamaldehyde is an aldehyde, thats a bit a difference isn´t it?

confused
/ORG




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[*] posted on 6-8-2006 at 11:55


Excuse me for being unclear.

I was talking about reducing the acids to alcohols with LiAlH4 or NaBH4 and using HI to reduce the alcohol. Usually this second reduction is done in multiple steps by protecting the amine, tosylating the alcohol, cleaving the ester and finally deprotecting the amine. I always assumed it is done this way because rP/I reductions don't work on primary alcohols, but maybe there are different reasons...
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[*] posted on 6-8-2006 at 12:58


At least phenylalaninol is commercially available without problems AFAIK.

About the possibilty to reduce phenylalaninol with HI are conflicting reports, on the Hive it was claimed possible but others were not able to reproduce it. By theory HI is able to do this. Protecting the amine by methylation with formaldehyde might be a good idea though - to preserve the amine under the harsh conditions necessary and resulting in a more active product.

/ORG




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[*] posted on 6-8-2006 at 13:21


Phenylalaninol (or the HCl salt) could be reacted with SOCl2 and the hydrochloride salt of the formed chloride reduced with Zn/acetic...



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[*] posted on 6-8-2006 at 18:09


obsolete.

[Edited on 7-8-2006 by Organikum]




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[*] posted on 7-8-2006 at 03:29


Quote:
Originally posted by turd
Quote:
Originally posted by Sandmeyer
including phenmetrazine

Interesting compound. What about the aminoethanol derivate (2-phenylmorpholine), is it pharmacologically active?


Interestingly there is nothing on its pharmacology in the literature. That’s kind of weird given that its 3-methyl analogue is such a strong stimulant. The pharmaceutical companies trafficking phenmetrazine surely tested 2-phenylmorpholine on animals as well, but these companies rarely release much about their development research.

However, a certain somebody prepared 2-phenylmorpholine hydrochloride and tested it at 80mg. This somebody said it was one of the most annoying drugs he ever tried. It was psychoactive to some mild degree, but the most pronounced effect was of an extreme feeling of tiredness, kind of like due to a drop of blood pressure. So if the psychoactivity mechanism included any catecholamines release, its consequences were not noted because the subject was sedated from tiredness. The subject said its unpleasantness can only compare to drugs like opiates or benzodiazepins and these would even leave a better impression as it is always better to be put down due to psychological and not physiological activity.
At least it is ridiculously easy to prepare from styrene in a couple of steps, but what a stupid poison!




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[*] posted on 7-8-2006 at 03:45


Quote:
Originally posted by Sandmeyer
A quick scifinder litt search revealed that the existing methods to that compound are not too good IMO, if I was to make it from propiophenone I'd take propiophenone alpha brominate it, swap the bromine with ethanolamine, reduce the keto function with NaBH4 and treat the diol with HCl to construct the morpholino moity. But since I will never brake the law it's up to someone with the propper license to test the route in practice.


Actually, there already exist a couple of patents describing this route to phenmetrazine with the only difference in that H2SO4 is used in the cyclisation step. I hope anybody isn't going to bother asking for numbers as I believe those who are not motivated enough to do their own literature search should stay away from stimulants. To imagine that some irresponsible hillbilly who never made a single step inside a library can nowadays sell homemade meth! :mad: Lazy bastards should end up on opiates instead, thus contributing to the human evolution. :P




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[*] posted on 7-8-2006 at 06:08


Quote:
Originally posted by Nicodem

Actually, there already exist a couple of patents describing this route to phenmetrazine with the only difference in that H2SO4 is used in the cyclisation step.


Strange, when I did a scifi search I got some crappy method from a Bulgarian? group, I might have had the patents-off filter on...




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[*] posted on 3-10-2006 at 21:10


the phemetazine process orginally was from 2-hydroxylethylnor-ephedrine however that was prepared, probably exactly the way you describe with bromopropiophenone and ethanolamine. . the other processes involve the reaction of nor-ephedrine with oxalyl chloride then reduction with LiAlH4 then cyclization with H2SO4, or reaction with chloracetyl chloride treatment with a base, reduction and then cyclization with H2SO4. I was wondering if a simpler route to the intermediate would be treatment with 2-iodoethanol of norephedrine. of couse you would have multiple substitution by-products in this case you would use a stochiometric excess of amine to suppress the formation of tertiary and quaternary amines, but distillation would deal with this.
that's how phendimetrazine is made by reaction with 2-iodo ethanol on ephedrine then cyclization, phendimetrazine isn't as euphorogenic as phenmetrizine the old BI-62s
a method I think organikum might be interested in is the reaction of ethanolamine with phenylacetylcarbinol to get the shiff's base (this can also be isolated as a cyclic intermediate by dehydrating over silica and extaction) this can be reduced to the 2-hydroxynorephedrine and cyclized to some prized goods.


[Edited on 4-10-2006 by jon]

[Edited on 4-10-2006 by jon]

[Edited on 5-10-2006 by jon]

[Edited on 5-10-2006 by jon]
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[*] posted on 10-8-2008 at 23:04


Was any of these methods ever confermed ?

Ergo's write up dose look good tho.
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