One-Pot Double Oxidation Synthesis of N-1-Piperidonyl Amides From N-1-Piperidinyl Amides with meta-Chloroperbenzoic Acid: Rimonabant Analogue as Model Study

Abstract

A simple and efficient one-pot oxidation synthesis of N-1-piperidonyl amides was successfully developed through the double oxidation of hydrazides (involving hydrazonium formation, azodioxy-carbonyl compounds generation, and α-carbon oxidation) by using meta-chloroperbenzoic acid (mCPBA). The convenient oxidation method was also extended to Rimonabant analogue. The lactam oxidized Rimonabant analogue was first successfully synthesized for demonstrating the construction and characterized by NMR spectroscopic methods and the single-crystal X-ray diffraction study (ORTEP).

Keywords: N-1-piperidinyl amide; N-1-piperidonyl amide; Rimonabant analogues; mCPBA; oxidation.