Preparation of Optically Active Secondary Amines by Thermal Decomposition of (Methylbenzyl)urea Analogs: Absolute Configuration of (+)- and (−)-Mecamylamine. Preliminary Communication

Thermolysis of the (α-methylbenzyl)urea diastereoisomers 4 and 5 of (±)-mecamylamine ((±)- 1 ) and 6 and 7 of (±)-1-noreseroline O-methyl ether ((±)- 3 ) in refluxing alcohol afforded optically pure amines in high yield, besides optically pure carbamates of (α-methylbenzyl)amine which can be recycled. The absolute configuration of (?)-mecamylamine hydrochloride ((?)- 1 · HCl) was determined by X-ray diffraction analysis.