Synthesis, configuration, and dehydration of some 1-alkyl- and aralkyl-3-methyl-4-o-tolylpiperidin-4-ols

Abstract

Diastereoisomeric 3-methyl-4-o-tolylpiperidin-4-ols, derived from 4-piperidones, have been separated and their configurations have been established on the basis of ¹H n.m.r. data and their behaviour towards dilute hydrochloric acid. The isomeric dehydration products of these alcohols have been separated and their slow rates of equilibration, in comparison with those of 4-phenyl analogues, have been demonstrated. The ratios of the 3- and 5-methyl-tetrahydropyridines derived by treatment of the 4-o-tolylpiperidin-4-ols and related tertiary alcohols with acid are reported and discussed.