Synthesis of the Antidepressant Zimelidine and Related 3-(4-Bromophenyl)-3-(3-pyridyl)allylamines. Correlation of their Configurations.

Abstract
Various methods for the synthsis of the antidepressant (Z)-3-(4-bromophenyl)-N,N-dimethyl-3-(3-pyridyl)allylamine[zimelidine] are described. Syntheses of the analogous secondary and primary amines, as well as the corresponding tertiary, secondary and primary E-isomers are shown. The steric interrelations of these amines are discussed on the basis of chemical and spectral evidence (NMR, UV).