(2-Acetamidophenyl) cyclohexyl methanone → (2-Aminophenyl)(cyclohexyl)methanone

Participants

Reaction Steps

A solution of (2-acetamidophenyl) cyclohexyl methanone (0.53 g, 2.16mmol) in methanol (5 ml) and concentrated hydrochloric acid (15 ml) was heated at 80° C. for 1 hour. After this time the solution was cooled to ambient temperature and the solvents removed in vacuo. The residue was dissolved in water (10 ml) and basified with 4N sodium hydroxide solution (20 ml). The mixture was then extracted into ethyl acetate (4×20 ml) and the organic layers combined and dried (MgSO4). The solvent was evaporated and the residue chromatographed on silica in 2:1 petrol:ethyl acetate, to afford the amine (0.40 g, 91%) as a white solid. mp 73°-75° C. 1H NMR (360MHz, CDCl3) δ1.23-2.09 (10H, m), 3.27 (1H, m), 6.29 (2H, brs), 6.64 (2H, m), 7.25 (1H, dt, J=6 and 1Hz), 7.76 (1H, dd, J=7 and 1Hz).

Provenance & Evidence