Multi-Component Reactions of Aldehydes, Amines, and Ketones I. Synthesis and Crystal Structure Elucidation of a Novel Product of Condensation of Salicylaldehyde, 1-Methyl-4-piperidone, and Methylamine

Abstract

The condensation of salicylaldehyde, 1-methyl-4-piperidone, and methylamine has been studied as a model reaction. It was found that at a molar ratio of salicylaldehyde: 1-methyl-4-piperidone = 2:1 and an excess of methylamine the previously unknown heterocyclic compound 2-(3,6,13-trimethyl-1,2,3,4,4a,5,6,7-octahydro-7,12a-epiminopyrido[4,3-b][1,5]benzoxazocin-5-yl)-phenol was formed; its structure was elucidated by spectroscopic methods and X-ray analysis. A reaction pathway for this new multi-component condensation is suggested and discussed.