Spectroscopic study of some condensed piperidine bicyclanols

Abstract

The infrared and 1H and 13C NMR spectra of 3-phenethyl-3- azabicyclo [3.3.1] nonan-9-α(β)-ol (Iα and Iβ) and 8-phenethyl-8-azabicyclo [4.3.1] decan-10α-ol (II) have been examined in several media. The NMR data for I show that this compound has crystallized as an epimeric mixture of Iα and Iβ. Both structures adopt in CDCl3 and (CD3)2SO solution a flattened chair-chair conformation with the phenethyl group in equatorial positions with respect to the flattened piperidine ring. The IR spectra show the existence of intermolecular hydrogen bonding (presumably OH⋯N) in solid state. The NMR data for II indicate that both OH and phenethyl groups are in equatorial positions. The IR and Raman data for this compound in solid state indicate OH⋯N intermolecular hydrogen bonding. © 1988.