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by Eleusis
While surfing the library database (what most of you ought to be doing instead of cruising those alt.binary
groups) I came upon a tasty little process of considerable academic interest.
One of Dan Haney's little pets is the Mitsunobu Reaction, and finally I got around to looking it up. It deals
with the conversion of alcohols to azides, which can then be conveniently reduced to amines with a
variety of reagents (NaBH4 seems to be the most popular, but Al-Hg would surely do the trick).
This is fine for producing heavy mixed aryl/alkyl systems, like MDA, but extremely hazardous for
producing, say, methylamine, as the intermediate Methyl Azide is exceedindly unstable (ie - it tends to
explode) and to make matters worse, alkyl azides generally boil at ridiculously high temperatures.
Personally, I'd rather make HCN without a bodysuit, but then again...
Some inventive and entrepeneurial chaps at the University of Newcastle-upon-Tyne in the UK came up
with a one-pot process that goes straight from an alcohol to the amine hydochloride salt. You can't get
more direct than that for some of those more interesting compounds. Unfortunately, this is not a viable
way (as far as I can tell) to produce MDMA, or any other methylaminated compound, as it does not tack a
methyl group on with it. The advantage in using this to prepare MDA is that it will not produce any di- or
tri- aminated product, as an Al-Hg reduction (or any other similar mode of preparation) will do. As well,
there is no need to supply ammonia either in salt or aqueous form, though would be the least of worries to
me in the matter.
The overview follows, with a reference to chase at the end.
References
1. Preparation of Hydrazoic Acid: Org. React., 3, 327, 1947
2. Alcohols to Amines: Synthesis, Feb. 1987, pg 190-192
*DISCLAIMER* Remember, this is for academic purposes only.