HCID 60628064, compound → HCID 69219298, compound

Participants

Reaction Steps

The mixture of [4-(3-aminopropyl)-1-phenyl-cyclohexyl]-dimethylamine (380 mg, 1.46 mmole) was added to a solution of [2-(1H-indol-3-yl)ethyl]carbamic acid phenyl ester (409 mg, 1.46 mmole) in dioxane (10 ml). The batch was then refluxed for 12 h. Working up was performed by removing the dioxane by distillation 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 (5 ml) and dried with Na2SO4. The solvent was removed by distillation under a vacuum. The residue was the diastereoisomeric mixture of 1-[3-(4-dimethylamino-4-phenyl-cyclohexyl)-propyl]-3-[2-(1H-indol-3-yl)-ethyl]-urea, which was separated and purified by flash chromatography on silica gel (70 g). Methanol/EE (3:1, 1500 ml; 1:1, 500 ml; and 1:2, 1000 ml) was used as eluent. The more nonpolar diastereoisomer of 1-[3-(4-dimethylamino-4-phenyl-cyclohexyl)-propyl]-3-[2-(1H-indol-3-yl)-ethyl]-urea (Example 35, 95 mg, m.p. 126° C., 15%) and the more polar diastereoisomer of 1-[3-(4-dimethylamino-4-phenyl-cyclohexyl)-propyl]-3-[2-(1H-indol-3-yl)-ethyl]-urea (Example 36, 116 mg, m.p. 57° C., 18%) were isolated in this manner.

Provenance & Evidence