I read in Shulgin's book 'TIKHAL' that he alkylates tryptamines with different alkyl halides like bromoethane, methyl iodide.
But he frequently uses di-isopropyl ethylamine as a proton acceptor.
And I was wondering why he does'nt use triethylamine, like they use as a proton acceptor in acyalation reactions involveing acyl halides.
I therorize that the two isopropypl groups sterically interfere with tetra-alkammonium halide formation, from the alkyl halides present in the system, which would be an unwanted variable in this system.
Anyone have any insight?