Application of high-performance liquid chromatographic chiral stationary phases to pharmaceutical analysis : Direct enantiomeric resolution of amide derivatives of 1-phenyl-2-aminopropane

Abstract

A series of amide derivatives of the enantiomers of 1-phenyl-2-aminopropane (amphetamine) were resolved by high-performance liquid chromatography on a chiral stationary phase (CSP), ( R)-N-(3,5-dinitrobenzoyl)phenylglycine, which is commercially available in ionically and covalently bonded columns. The separation factor ranged from 1.01 to 1.09 and was consistently larger when the compounds were chromatographed on the covalent column. Chromatographic parameters correlate in detail with a solute-CSP interaction model requiring up to four binding sites and a fifth repulsive interaction which is steric in origin and which provides the key chiral discriminant.