Synthesis of 1-(3-aminopropyl)indoles and 3-indol-1-ylpropionic acids

Abstract

Various substituted indoles and their derivatives have been condensed with acrylonitrile in the presence of trimethylbenzylammonium hydroxide to give the corresponding 3-indol-1-ylpropionitriles. These nitriles were reduced catalytically with Raney nickel to the corresponding 1-(3-aminopropyl)indoles, or hydrolysed to the corresponding 3-indol-1-ylpropionic acids. Some of the nitriles were formylated to give the corresponding 1-(2-cyanoethyl)indole-3-aldehydes.