Pyridine → (4-Dimethylamino-4-phenylcyclohexylmethyl)-carbamic acid phenyl ester

Participants

Reaction Steps

The chloroformic acid phenyl ester (1.32 ml, 10.5 mmole) dissolved in abs. DCM (25 ml) was slowly added dropwise while cooling with iced water to a solution of (4-aminomethyl-1-phenylcyclohexyl)-dimethylamine (2.32 g, 10 mmole) in abs. DCM (25 ml) and pyridine (888 μl, 11 mmole). The reaction mixture was then stirred for 20 hours at RT. The reaction mixture was worked up by extraction with water (3×10 ml), with 1M HCL (3×10 ml) and with 1M NaOH (2×10 ml). The organic phase was dried with Na2SO4 and then concentrated by evaporation. The residue was the diastereoisomer mixture of (4-dimethyl-amino-4-phenylcyclohexylmethyl)-carbamic acid phenyl ester. This was obtained as a colourless solid in a yield of 3.18 g (m.p. 108°-124° C., 90%).

Provenance & Evidence