HCID 12986252, compound → HCID 10025689, compound

Participants

Reaction Steps

The diastereoisomer mixture of (4-aminomethyl-1-phenyl-cyclohexyl)-dimethylamine (465.8 mg, 2.0 mmole) was added to a solution of (3-phenylpropyl)carbamic acid phenyl ester (510.6 mg, 2.0 mmole) in dioxane (15 ml). The batch was then refluxed for 12 h. Working up was performed by removing dioxane by distillation in a rotary evaporator and combining the residue with water (10 ml). The batch was adjusted to pH 11 with 5M NaOH and extracted with EE (3×20 ml). The combined EE extracts were washed with 1M NaOH (1×5 ml) and dried with Na2SO4. The solvent was removed by distillation under a vacuum. The residue was the diastereoisomer mixture of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-(3-phenyl-propyl)-urea, which was separated and purified by flash chromatography on silica gel (60 g). Ethanol/EE (1:1, 1100 ml) was used as eluent. The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-(3-phenyl-propyl)-urea (310 mg, yellow oil, 39%) and the more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-(3-phenyl-propyl)-urea (55 mg, m.p. 159-165° C., 32%) were isolated in this manner.

Provenance & Evidence