rac-(1R,2R)-2-phenylcyclopentan-1-amine hydrochloride → cis-2-Cyclohexylcyclopentylamine hydrochloride

Participants

Reaction Steps

Using rhodium-on-charcoal catalyst in a Paar shaker, 12.6 g of cis-2-phenylcyclopentylamine hydrochloride, M.P. 204°-206° C in 100 ml of water is hydrogenated. In 20 hours when the theoretical amount of hydrogen has been taken up the catalyst is removed by filtration, the filtrate made basic with sodium hydroxide solution, and the resulting precipitate is extracted into ether. After evaporation of the ether the residue is distilled, M.P. 100°-102° C (6.0 mm). The hydrochloride salt is prepared and recrystallized from isopropanol-ether to give 4.4 g of cis-2-(cyclohexyl)cyclopentylamine hydrochloride, M.P 174°-176° C.

Provenance & Evidence