I believe "Hofman Alkylation" is the proper term for what I am going to describe.
I always thought reductions in the manufacture of amphetamines were a bit silly.
I mean, ephedrine or pseudoephedrine can be had, however, allyl or propenyl benzenes are plentiful and cheap.
I can't recall the Markovnikov rule right off the top of my head, I think it goes that the halide goes to the carbon with the most hydrogens. Why not convert the phenylalkene to a phenylalkyl halide with HX, then alkylate N-methylacetamide (would the alkyl group be more likely to alkylate the nitrogen or the keto-oxygen?), removing the acetyl group afterwards, or not (would it make a difference? I know N-acetyl tyrosine is more potent in it's effects than non-acetyl).
Or, the Gabriel synthesis. The phenylalkyl halide + potassium phthalimide in dry alcohol. On this one, I know hydrazine is dangerous, would arginine work to de-phthalate the product, or, again, would it make a difference except in weight/potency? Would calcium or sodium (or potassium) remove the acyl group?
Substituted allyl/propenyl benzenes are present in essential oils, thus are highly available.
What was the final word, btw, on the Delepine reaction. I've heard yes, no, it only works on this or that.
James