A Simple Synthesis of 5-Amino-3-(2-dimethylaminoethyl) indole [5-Amino-N,N-dimethyltryptamine]

Abstract

A short (three step) synthesis of 5-amino-3-(2-dimethylaminoethyl)indole [5-amino-N, N-dimethyltryptamine, 4] from commercially available starting materials is presented. Reaction of 5-nitroindole with oxalyl chloride followed by dimethylamine afforded N,N-dimethyl 5-nitroindole-3-glyoxamide (1), which was reduced by diborane to 5-nitro-3-(2-dimethylaminoethyl)indole (3). Catalytic reduction of (3) afforded the title compound in 19% overall yield from 5-nitroindole.