Studies on Spasmolytics. II. Synthesis and Anticholinergic Activities of 4-Acyloxy-1-alkyl-1-(1, 3-dioxolan-4-ylmethyl) piperidinium Compounds

Abstract

Quaternization of 4-acyloxy-1-(1, 3-dioxolan-4-ylmethyl) piperidine derivatives with methyl bromide afforded two diastereoisomers in equal amounts. The stereochemistry of these compounds was determined from the chemical shift of the N-methyl signals in the proton nuclear magnetic resonance (¹H-NMR) spectra. The quaternary salts showed high anticholinergic activities. The trans isomers tended to be more potent than the corresponding cis isomers.