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

Authors:
  • MIM. A. Iorio
    M. A. Iorio
  • ACA. F. Casy
    A. F. Casy
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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.