just found that after posting that one
All my chem knowledge just fell out of my head. ketone: double bonded oxygen with carbons either side on the chain, aldehyde, with just a hydrogen on one side and a double bonded oxygen... ie ketone is not on a terminal carbon, aldehyde is... I know you know that. I forgot.
Wouldn't it be tryptophol then if IAA was fully reduced?
and I spotted this one on the tryptophol synthesis page:
N-disubstituted tryptamines are obtained in high yield on boiling a solution of tryptophols in benzene or xylene with secondary amines and a nickel catalyst.nice
so how does this sound -
IAA --> tryptophol via Ni catalyst or other gentle reduction.
tryptophol + dimethylamine --> dmt via nickel catalyst
would that work? would it be best catalytic or high-pressure?
have I read this all wrong? It sounds too easy. I can't seem to find any info on IAA->tryptophol, but it seems reasonable.
It'd be nice for the factor of being able to use cheap ass urushibara, which is said to be quite a gentle reducing agent.