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Author: Subject: Amino alcohol via Akabori, trial run
swip2
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[*] posted on 12-2-2008 at 22:12


Swip2 dident notice wether diffrent solvents can be used, And whitch ones work better.

Swip2 assumes an avarige non polar solvent would do for the post reaction work up :(
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manimal
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[*] posted on 17-2-2008 at 12:58


Sodium carbonate can be used to base ephedrine or norephedrine, but isn't strong enough to base benzylamine because benzylamine can form a carbonate salt whereas ppa cannot, no? So wouldn't the addition of a carbonate seperate the ppa as a freebase, but not the benzylamine, which forms a carbonate?
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swip2
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[*] posted on 17-2-2008 at 18:50
PPA Sulphate or Citrate maybee


Quote:
Originally posted by IOC
Try alanine/benz, heat directly, when CO2 is done add equal amount of toulene then add equal amount of H2O and acidify to PH 4, seperate water phase and 3 x methylene chloride to clean.

Boil down H2O pahse to a brown paste then add dry acetone to leave clean white powder.

Havnt had time to qualify MP, next time though

IOC......out


So how about a PPA Sulphate or a citrate salt.
Swip2 just isent sure weather a sulphate salt would reduce to the desired amine

[Edited on 18-2-2008 by swip2]
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Nicodem
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[*] posted on 19-2-2008 at 11:16


From here on no more schizophrenic third person writing or use of acronyms of the SWIM-type will be allowed. Any other methods of posing or pretending of being involved in some criminal activities, or similar childish attempts at being kewl, are also not desired.

Any post not respecting the above will be deleted.

This warning is valid in general and not just this thread.

This used to be a very nice and informative thread about an interesting reaction. Do not deteriorate it! If you have nothing useful to add, then rather think twice before posting.
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[*] posted on 19-2-2008 at 23:41


sorry tar.gz was ment to mean tar ball :) I was in a hurry and should have thought more about my post.



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stoichiometric_steve
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[*] posted on 20-2-2008 at 03:22


i was about to complain, too. maybe some cleanup should be done here. from page 2 it's mainly bullshit being posted.
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LSD25
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[*] posted on 24-2-2008 at 15:52


Quote:
Originally posted by Nicodem
From here on no more schizophrenic third person writing or use of acronyms of the SWIM-type will be allowed. Any other methods of posing or pretending of being involved in some criminal activities, or similar childish attempts at being kewl, are also not desired.

Any post not respecting the above will be deleted.

This warning is valid in general and not just this thread.

This used to be a very nice and informative thread about an interesting reaction. Do not deteriorate it! If you have nothing useful to add, then rather think twice before posting.


Done,

All non-informative and cookery related material that I have access to is now deleted and will not return.

This should please Sauron & Polverone no fucking end.

Out




Whhhoooppps, that sure didn't work
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Nicodem
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[*] posted on 24-2-2008 at 23:23


I don't know what you are up to, but your posts were one of the few here that did not fit the criteria for removal. Besides, the warning was set for 19/2/2008 and forward and not for already posted material. Take notion that his is not a thread where you can demonstrate your political opinions by performing irrational acts!

Edit: Now that I think of it, you are actually trying to be kewl if the definition of kewlness is stretched a bit. Maybe your above post actually breaks the anti-kewls rule after all. I'll have to think about it and perhaps remove it.

[Edited on 25/2/2008 by Nicodem]
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azo
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[*] posted on 7-3-2008 at 14:37
akabori


I was looking at the akabori reaction and come up with the idea of reacting phenylalinine with formilin the reaction seems to follow the same mechanism as the benz method only that the end product would be 1 phenyl 2 amino propane 3 ol . The only thing that i thought would be getting the temperature high enough to decarboxylate the phenylalinine due to the boiling point of water
and the reactivity of the formaldehyde which is a lot more reactive than benzaldehyde
if it would work i thought it would give a better yield due to the solubility of phenylalinine and formilin and easier for the workup with less tar.
has anyone seen this reaction before and do you think it is possable

regard azo
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Maja
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[*] posted on 28-4-2008 at 10:11


Retried Akabori reaction with Benzaldehyde and Alanine... This time I used overhead stirrer and kept temperature 150-165* for about 2hours. Some benzylamine and other products distilled over 2hours, but not a lot of. OK ... This is phase were I faced some problem.. Tried to extract with toluene... And guess what ? No layers ... Just brown solution with no layers. Emulsion ? I don't think so... Maybe someone knows how to solve this problem ?
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[*] posted on 28-4-2008 at 19:28


Quote:
Originally posted by Maja
Retried Akabori reaction with Benzaldehyde and Alanine... This time I used overhead stirrer and kept temperature 150-165* for about 2hours. Some benzylamine and other products distilled over 2hours, but not a lot of. OK ... This is phase were I faced some problem.. Tried to extract with toluene... And guess what ? No layers ... Just brown solution with no layers. Emulsion ? I don't think so... Maybe someone knows how to solve this problem ?


There really aren't any layers. The toluene is mostly to thin things out a bit so it will be easier to filter out the unreacted alanine and maybe some tar etc. The last time I tried this (quite a while back) I just filtered the thinned solution a few times to clean it up as much as possible and then added water and HCL to extract the reaction product. That's really the only time I saw any kind of layers form. I never really had much of a tar layer at the bottom.
Once the water has been evaporated, the amine salt is left behind as a dirty paste (Just like in the photos) and is kind of a bitch to clean up, but it can be done.

As an aside, I seem to remember having VERY strong ammonia-like vapors coming from the reaction solution. I'm not sure if this was from a lot of benzylamine (or other side products) forming, or if it was just from the amine that that was the desired product of the reaction.


**I almost forgot...After the aqueous layer has been separated, be sure to wash it several times as well as you can with a non-polar solvent. DCM definitely works best for this if you have it. Otherwise it'll take a ton of ethyl acetate to clean up the paste at the end.
Pretty much everything Cycloknight put in his write up works the way he says it does if you follow his procedures.

[Edited on 29-4-2008 by Hilski]




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azo
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[*] posted on 28-4-2008 at 20:00


? what isomer is produced by the akabori is it norephedrine
or norpseudoephedrine.
I haven't heard it mentioned

thanks azo.:)
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Maja
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[*] posted on 29-4-2008 at 11:23


Oh, I see... So why does he state that you need to extract with toluene ? :] I will try what you said. I have DCM. I don't actually remember from the past if there was layers or no ..

I think it's norpseudoephedrine if IIRC :]

[Edited on 29-4-2008 by Maja]
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Hilski
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[*] posted on 29-4-2008 at 16:01


Quote:
Oh, I see... So why does he state that you need to extract with toluene ? :] I will try what you said. I have DCM. I don't actually remember from the past if there was layers or no ..

I think it's norpseudoephedrine if IIRC :]


I'm not really sure why he used the term 'extract' when referring to the procedure right after the reaction completes. I believe it's just semantics, and I THINK what he was intending to convey was that one just needs to add toluene to the final reaction mixture. Then filter out the unreacted alanine and wash the alanine with some clean toluene to make sure no product is left behind. Then pool all the toluene together to do the the extraction on the toluene with aqueous HCL.

If I'm not mistaken, the reaction product is a mixture of d- and l- norephedrine, a.k.a phenylpropanolamine. There might also be some norephedrine in there too, but I don't think so.




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[*] posted on 1-5-2008 at 19:03


benzylamine is only formed about 1-3% it is soluble in h2o completely not an issue. diphenylethanolamine is insoluble in alcohol as a base per a scientist at sigma aldrich .6g/100ml with heavy sonification. this is the major impurity.
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[*] posted on 17-5-2008 at 20:44


So Maja, any luck? I'm just curious, because I don't remember reading any posts by anyone other than Cycloknight who actually tried the experiment and got it to work . IIRC I ended up with %15-%20 yields (based on benzaldehyde) when I did it last.



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HeilHamas
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[*] posted on 11-11-2008 at 19:37


Quote:
Originally posted by jon
I've given the serine route a thought but after some research I concluded it may or may not be possble because of the steric factors involved with alanine the carbon bearing the alpha hydrogen is substituted in alanine in the case of glycine it is not.

[Edited on 23-12-2007 by jon]


It's been demonstrated to work for alanine and nitrobenzaldehyde in an uncatalyzed reaction. Nitrobenzaldehyde is more reactive in such reactions, but if steric hinderance doesnt hinder alanine and nitrobenzaldehyde, why would it hinder alanine and benzaldehyde? It should be tried in a standard base-catalyzed reaction.
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chochu3
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[*] posted on 14-11-2008 at 20:41


PPA*HCl
very sol. H2O
sol. Alcohol
insol. ether, benzene, chloroform

PPA freebase
sol. ether

Alanine
sol. H2O
slightly sol. Alcohol, pyridine
insol. Acetone, ether

Best way to workup this reaction would be to do the extraction with ether so it will solvate the PPA and leave the alanine behind. Referenced from Handbook of Chemistry and Physics 85th edition except the solubilty of the phenylpropanolamine freebase which was read from a patent online here




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[*] posted on 4-12-2008 at 08:03


there is no way for convert ppa to pesudoehedrine?
i think if we use methyle alanine then we will have pesudoephedrine




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hector2000
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[*] posted on 21-12-2008 at 10:14


why final product has tart and bitter taste?



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sk13m11
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[*] posted on 26-3-2009 at 07:39
l-alanine to ppa


can i use beta-alanine instead of l-alanine
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[*] posted on 27-3-2009 at 03:55


@ sk13m11 - You can use l-alanine, d-alanine or dl-alanine. NOT BETA (B)!

@ hector2000 - The original Akabori (and MOMOTANI) paper trials n-methyl alanine (thats the whole point of the paper, semi synthetic ephedrine). They got 16% with there method which uses pyridine. The methods you read on this site increase the yield and dont use pyridine. Although since n-methyl alanine is not commercially available no one as tried it since Akabori...
You can methylate an amine (single methylation) with formaldehyde and a reducing agent.

Products via this method are racemic (4 different isomers).

[Edited on 27-3-2009 by Siddy]
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sk13m11
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[*] posted on 31-3-2009 at 02:17


thanks for the info
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[*] posted on 21-5-2009 at 14:44


Sorry, under a new pseudonym (while I try and find my original activation email - I suspect it is in an account which has been heavily spammed).

Found this the other day, it is in Japanese too, but it at least shows a putative reaction scheme (via an acid labile, 5 membered ring). Interestingly, it claims that the 3,4-MD benzaldehyde (piperonal) gives up to 87% yield while plain old benzaldehyde gives only <50% (which is likely, given that it forms two sides of the 5 membered ring).

The references from this paper really ought to be rather special reading if anyone can find them too:cool:

Attachment: akabori.rewrite.2007.pdf (94kB)
This file has been downloaded 1892 times

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Siddy
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[*] posted on 21-5-2009 at 17:41


good find no1uwant2no,

You can get a ruff translation from google, and make sense of it.

But it doesnt detail the method, or say how the yield was increased.
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