Synthesis and reactions of N-indol-3-ylmethylalkylammes and related compounds

Abstract

A series of new N-indol-3-ylmethylalkylamines (1) have been synthesized in excellent yields via transamination between gramine and the appropriate primary alkylamine. The use of tryptamine and propane-1,3-diamine in the exchange reaction afforded N-indol-3-ylmethyltryptamine (2), and N,N′-bis(indol-3-ylmethyl)propane-1,3-diamine (3) respectively, whereas the use of methylamine gave N,N-bis(indol-3-ylmethyl)methylamine (4). The exchange reaction has been extended by the use of amino acids to give N,N-bis(indol-3-ylmethyl)tryptophan (6) and N,N-bis(indol-3-ylmethyl)glycine (8). The secondary amines (1), (2) and the previously known bis(indol-3-ylmethyl)amine proved to be valuable intermediates for the synthesis of some new compounds related to gramine as well as to other indole alkaloids.