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Globey
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[*] posted on 7-10-2010 at 04:58
hydrocarbon to alcohol


This probably should be in the newbie thread: if one wanted to turn a clearly controlled compound like d-methamphenamine in a legal, medically useful, OTC one, l-ephedrine, could that easily be accomplished through simple oxidation? Perhaps permanganate in (aq) NaOH, and the freebase hydrocarbon oil would precipitate maybe as a flocculent, slightly flaky waxy powder to the bottom. Just wondering weather it is possible for one to make something legal, legitimate OTC usage (yet watched), out of something clearly controlled. Want to give more options to those who may legitimately feel stuck in a horrible addiction. Thanks for listening, and please refrain from being anti-social like responses. Sorry, and many thanks for the help, in advance! You know, l-ephedrine was almost the perfect asthma medication for many, and it gave just the right amount of stimulation without driving one's brain into some sort of synthetic crack heaven. Tried to utFse, but it wouldn't put out for me, and I didn't feel like raping it. Arr ar ar. You cn kill me now;
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DDTea
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[*] posted on 7-10-2010 at 05:17


Bahahaha, I like this idea a lot. Reverse meth lab, turning crank into legal substances! I'd LOVE to see the faces of the DEA agents that raid such a lab...

How about free-radical bromination of the methamphetamine (ideally, leading to significant quantities of a benzylic bromide) followed by a nucleophilic substitution by water?

[Edited on 10-7-10 by DDTea]




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Globey
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[*] posted on 7-10-2010 at 05:41


Quote: Originally posted by DDTea  
Bahahaha, I like this idea a lot. Reverse meth lab, turning crank into legal substances! I'd LOVE to see the faces of the DEA agents that raid such a lab...

How about free-radical bromination of the methamphetamine (ideally, leading to significant quantities of a benzylic bromide) followed by a nucleophilic substitution by water?

[Edited on 10-7-10 by DDTea]


Let's keep this serious. Having the amine gone is obviously a non-starter. Might be suicidal to try it on a micro-scale only if I had any of the hydrocarbons, but I never have even had any of them. The closest I came was 26 years ago when I got a little bit from the old Vicks inhaler (the l form of deoxyephedrine).

I see no reason why this Rxn might not work under powerful, dilute conditions. The freebase precipitating as a solid out of the way would help to make purification all the easier. recrystallization in a slightly impure aqueous medium. I am absollutely no chem guru, this is just a simple inquiry and wondering if anyone might lend some constructive criticism. Thanks a bunch again!
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[Edited on 7-10-2010 by Globey]
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DDTea
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[*] posted on 7-10-2010 at 06:44


No no, I wasn't proposing that you get rid of the amine. I was proposing putting a bromide onto the benzylic carbon and then doing a nucleophilic substitution of the bromide thus formed.



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Globey
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[*] posted on 7-10-2010 at 07:16


Quote: Originally posted by DDTea  
No no, I wasn't proposing that you get rid of the amine. I was proposing putting a bromide onto the benzylic carbon and then doing a nucleophilic substitution of the bromide thus formed.


Do you see any drawbacks with the method I proposed? Aq NaOH- -MNO4 at perhaps pH10, reacting directly with freebase, oily hydrocarbon, and forming the corresponding alcohol freebase as a waxy solid which wold separate rather easily? Or would one need a far stronger base. The KMN04 might form the ketone while at it, which is also a no no. Maybe your nuclophylic substitution/swap is the best way. Then quenching with HOH to form the alcohol with a bromide left behind.

[Edited on 7-10-2010 by Globey]
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[*] posted on 7-10-2010 at 07:41


Oxidation of N-methylamphetamine with permanganate could utmost give phenylacetone or benzoic acid. You could in principle make the amide of glycolic acid from N-methylamphetamine, esterify it with HNO2, perform the Barton reaction, deoxymate, reduce the carbonyl to hydroxy and hydrolyse the amide. The reaction should have some good diastereoselectivity, so you would get one of the diastereoisomers of ephedrine as the major product. Obviously this would be one of the most stupid ways to such a simple compound, but since this is just a useless discussion, the proposal can be just as useless.
Alternatively, possibly trifluoroacetyl protected methylamphetamine (N-methyl-N-trifluoroacetylamphetamine) could be radically brominated with NBS to give N-methyl-N-trifluoroacetyl-1-phenyl-1-bromo-2-aminopropane. The nucleophilic substitution with acetate should give the N-methyl-N-trifluoroacetyl-1-phenyl-2-aminoprop-1-yl acetate which upon complete hydrolysis would give a mixture of ephedrins. Here too, a good diastereoselectivity can be expected. One of the problems could be the elimination of the bromide instead of the SN2 (acetate is not very basic in water, but in other solvents it can be).




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[*] posted on 7-10-2010 at 16:47


I like the idea of radical bromination with NBS because it is pretty simple and cheap (and in this case, it would be *really* silly to invest extra money into the reaction!) and the benzylic bromide should be favored, along with a tertiary bromide on C<sub>2</sub>. Of course, as Nicodem mentioned, protecting the amine group would be important.

Doing the substitution of the bromide under S<sub>N</sub>1 conditions might be worthwhile in this case (i.e., instead of doing the substitution with OH<sup>-</sup>, use H<sub>3</sub>O<sup>+</sup>.

The product would, of course, be a mixture of stereoisomers.

[Edited on 10-8-10 by DDTea]




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Globey
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[*] posted on 8-10-2010 at 11:12


Well, seems the experts here that be think there's no simple easy way to go from the hydrocarbon back to the alcohol. Way easier to go the other way around.
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[*] posted on 8-10-2010 at 18:43


Quote: Originally posted by Globey  
Well, seems the experts here that be think there's no simple easy way to go from the hydrocarbon back to the alcohol. Way easier to go the other way around.


Radical halogenation is one of the most piss easy things to do. You don't *really* need NBS, although it is much better in synthetic applications. You could do it just as easily with Br<sub>2</sub> in MeCl<sub>2</sub>.

You could probably use acetyl chloride to protect your amine rather than a trifluoroacetyl group.

The nucleophilic substitution should be easy and favorable, especially under S<sub>N</sub>1 conditions.

All that's left to do after that is hydrolyze the protecting group.

Where's the hard part?




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madscientist
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[*] posted on 8-10-2010 at 20:53


You're correct about it being harder to go from methamphetamine to ephedrine than vice versa.

Don't understand why you would want to do this, though. It's a lot easier, cheaper, and safer (legally and physically) to find some gas station that's ignoring the ban on ephedrine than to buy a bunch of meth!

Quote:
Bahahaha, I like this idea a lot. Reverse meth lab, turning crank into legal substances! I'd LOVE to see the faces of the DEA agents that raid such a lab...


No kidding. :D




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Globey
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[*] posted on 9-10-2010 at 09:11


Trud dat about the gas station. Nuno, was wanting to extrapolate going from easily avail PEA to phenylethanolamine. I think you could get this to the alcohol as well by using some cheap enzymes to hydrate it. I know your halogen swap is easy and enthropically favorable, at both steps probably exothermic.
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Globey
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[*] posted on 9-10-2010 at 09:12


Quote: Originally posted by madscientist  
You're correct about it being harder to go from methamphetamine to ephedrine than vice versa.

Don't understand why you would want to do this, though. It's a lot easier, cheaper, and safer (legally and physically) to find some gas station that's ignoring the ban on ephedrine than to buy a bunch of meth!

Quote:
Bahahaha, I like this idea a lot. Reverse meth lab, turning crank into legal substances! I'd LOVE to see the faces of the DEA agents that raid such a lab...


No kidding. :D


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[*] posted on 10-10-2010 at 08:09


^what is the purpose of this?

also if you wanted to oxidize PEA, why not just ask that in the first place?

[Edited on 10-10-2010 by spirocycle]
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Globey
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[*] posted on 12-10-2010 at 00:15


Quote: Originally posted by spirocycle  
^what is the purpose of this?

also if you wanted to oxidize PEA, why not just ask that in the first place?

[Edited on 10-10-2010 by spirocycle]


Yes, please tell, thanks. Definitely want to stop short of the acetophenone.
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Globey
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[*] posted on 12-10-2010 at 08:46


Quote: Originally posted by spirocycle  
^what is the purpose of this?

also if you wanted to oxidize PEA, why not just ask that in the first place?

[Edited on 10-10-2010 by spirocycle]


Sure, plese do tell. But I'd like a substituted ethanol as end product, and not a ketone. So I am asking now that of you spirocycle. 2-PEA to the corresponding alcohol;

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[*] posted on 12-10-2010 at 18:55


I'm not nearly skilled enough to help you with that oxidation.

it might be easier to oxidize it to the ketone, and then reduce it back to the alcohol.
just suggesting.
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Globey
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[*] posted on 13-10-2010 at 07:01


Quote: Originally posted by spirocycle  
I'm not nearly skilled enough to help you with that oxidation.

it might be easier to oxidize it to the ketone, and then reduce it back to the alcohol.
just suggesting.


I was thinking more the lines of precipitating the phenylethanlolamine (freebase) as scaly wax floculent from a non-polar, and before it has chance to form acetophenone.

If phenlethanolamine is insoluble in non-polar, clean-up of decently pure compound should be a cinch, as it will readily be tied up as solid, and hopefully at bottom (water is light). Any help appreciated. Thanks. This is actually an adaptation from an advanced organic lab experiment from a few semesters and I never got around to it, I'm curious. My lab mate was a born again, and he almost blew us up. NOT becuse of any specific unstable high energy he was er ertr producing (even he was far too dumb), but brsudr he did simplex with silicon lube on sopcpck on top of reflux cond., and managed to twist it on nice and tight!!!!!!!!! Makes me angry to think about cleaning up that pre-PCP. BTW, Quite Cool professor.
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[*] posted on 17-10-2010 at 05:51


Thanks to all, especially Nicodem (you've given me a treasure trove of possibilities, some very intriguing). Now to just find the time! ;)
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