Studies of stereochemical influences upon anti-histaminic activity. The synthesis, configuration, and anti-histaminic properties of some isomeric aminobutenes

Abstract

The acid-catalyzed dehydration of 4-dimethylamino-2-p-methoxyphenyl-1-phenylbutan-2-ol yields all four possible 4-amino-1,2-diarylbutenes. Pure samples of each isomer have been isolated, double bond positions and configurations being established from proton magnetic resonance and ultraviolet spectroscopic data. A stereoselective route to cis aminobut-1-enes has been further investigated. The anti-histaminic properties of the reported butenes together with some related compounds are given and structural influences upon activity discussed.