Synthesis and structural and conformational study of some amides derived from 3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-amine

Abstract

A series of amides derived from 3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonan-9-amine (I) have been synthesized and examined by IR, 1H and 13C NMR spectroscopy, and the crystal structure of 9-(3-indolycarboxamido)-3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane hydrochloride (IV·HCl) has been determined by X-ray diffraction. The 1H and 13CNMR data of the parent amine (I) are also included. These compounds adopt an almost perfect chair-chair conformation with the NCH3 groups in the equatorial position.