Stereochemical Studies of the 4-Alkyl-4-Arylpiperidine Class of Opioid Ligand

Article abstract of DOI:10.1002/mrc.1260271012

The (1)H (270, 400 MHz) and (13)C (67.5 MHz) NMR spectra of some 4-methyl- (also 4-n-propyl- and -isobutyl)-4-(3-hydroxy- and 3-methoxy-phenyl)piperidines and their 3-methyl diastereoisomers are reported.Many of the compounds had opioid ligand activities.The data were analysed in terms of preferred conformation and configuration (3-methyl derivatives).Only compounds with preference for axial 4-aryl chair conformations displayed marked agonist properties and the one potent antagonist, cis-1,3,4-trimethyl-4-(3-hydroxyphenyl)piperidine, favoured an equatorial 4-aryl chair. KEY WORDS 4-Alkyl-4-arylpiperidines Opioid ligands (1)H NMR (13)C NMR Stereochemistry Conformational analysis