Dicyclohexylamine → Dicyclohexylammonium chloride

Participants

Reaction Conditions

Reaction Steps

To a mixture of 755 mg (5.00 mmol) 4-(4-piperidyl) 1-H-imidazole and 942 mg (5.20 mmol) of dicyclohexylamine in 10 ml anhydrous acetonitrile at 25° C. was slowly added 1.06 g (5.20 mmol) cyclohexanevaleroyl chloride in 2 ml of dichloromethane over a period of 10 min with stirring; then the reaction mixture was heated at 60° C. for 1.5 h. After cooling to ambient temperature, the solid side product that was obtained (dicyclohexylammonium chloride) was filtered off and the filtrate was concentrated in vacuo to remove acetonitrile. The resulting crude oil was crystallized with methanol: anhydrous diethyl ether to give 1.085 mg of analytically pure product as a yellow powder. Yield: 68%; M.P.: 159° C.; MS: m/e=317(M+); 1H NMR (CDCl3): imidazole H: δ 7.65 (s, 1H), 6.75 (s, 1H); cyclohexylbutyl: δ 2.20 (m, 8H), 1.20 (m, 11H); piperidyl: 4.65 (d, 2H), 3.95 (d, 2H), 3.10 (d, 2H), 2.84 (m, 1H), 2.20 (m, 2H).

Provenance & Evidence