3-phenyl propionic acid + SOCl2 and an excess of ammonia to yield 3-phenyl propanamide which is reacted with LiAlH4 to yield amphetamine.

Does this sound feasible?

I think I remember hearing that sodium borohydride was easier to come by/make, could be it substituted for the reducing agent? I'll do more research tonight, I have work soon.

Also, is thionyl chloride difficult for those of us without special permissions to purchase? I'll look that up tonight, too, but if someone knows off-hand, it'll save me the time.

I'd love to see the dox on the 3/2 rearrangement of an amide, which would be win. I've heard it mentioned that such things are doable by some means, but not the how...

...I'd also probably form the acyl halide, purify, and react rather than try for a one-pot, but maybe not.

It wouldn't really rearrange, as far as I know, the amine would just replace the chlorine.

Mechanism. (http://www.chemguide.co.uk/mechanisms/addelim/ammonia.html#top)

And the thionyl chloride forms the acyl chloride, I suppose cleaning that up would be beneficial.

3-phenyl propionic acid + SOCl2 and an excess of ammonia to yield 3-phenyl propanamide which is reacted with LiAlH4 to yield amphetamine.

Does this sound feasible?

Sure, If you can make get SOCL2, LiALH4 (there are much better uses for it btw). But that is an interesting route, 3-phenyl propionic acid how is that going to be made?

I think I remember hearing that sodium borohydride was easier to come by/make, could be it substituted for the reducing agent? I'll do more research tonight, I have work soon.

Possibly but i doubt it. NaBH4 is easier to come by but remember. LiAlH4 is like a cannon and NaBH4 is a shotgun (as in reducing agent wise).

Also, is thionyl chloride difficult for those of us without special permissions to purchase? I'll look that up tonight, too, but if someone knows off-hand, it'll save me the time.

Yes, There are 2 places in the EU that sell it that i know of, but otherwise it is impossible to get :( You could make it, len1 has some great work on it on SM, look at that!

Good luck:)

It wouldn't really rearrange, as far as I know, the amine would just replace the chlorine.


I think the point Joe was making is that if you did this reaction, you would not get amphetamine, but rather 3-phenyl propylamine - a constitutional isomer...

http://www.evilshare.com/60ca532c-b1c3-102b-8834-0007e90cfb90

All right, well, first of all, I miscounted carbons, you'd need to start with 2-phenyl ethanoic acid (hence the whole phenethylamine thing), that was a gross oversight on my behalf. Starting with prop. acid wouldn't even lead to an isomer of amp, as there would be an extra carbon.

But, if fcknut and Joe could elaborate, I'm not quite sure I'm following.

Also, I have found sources which export the starting material and a separate company for thionyl chloride. I haven't had much luck finding a list of watched chems, though, so I don't know how worthwhile it would be to attempt to have it imported.

No, your original suggestion would lead to an (presumably inactive) isomer of of amphetamine , whereas the 2-phenylacetic acid would not - remember that there is an alpha-methyl group in amphetamine...

But, if fcknut and Joe could elaborate, I'm not quite sure I'm following.

Amphetamine is phenylpropyl-2-amine.

Your initial procedure would yield phenylpropyl-3-amine. Phenylethanoic acid would yield phenethylamine. Neither of these are phenylpropyl-2-amine.

Do an image search on the molecular structure. Might help. ;)

I'm retarded, I'll clean this up later.

I'm retarded, I'll clean this up later.

a-m(D/L)PA (http://www.cem.msu.edu/~reusch/VirtualText/crbacid3.htm)