4-(4-Chlorophenyl)-4-hydroxypiperidine → HCID 12043490, compound

Participants

Reaction Steps

3-[(9-Ethyl-9H-carbazol-3-ylcarbamoyl)-methyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-carbamic acid tert-butyl ester was synthesized similarly to example 44, substituting 3-aza-bicyclo[3.1.0]hex-6-yl)-carbamic acid tert-butyl ester for 4-(4-Chlorophenyl)-4-hydroxypiperidine and substituting the compound of example 19 for the compound of example 40. A solution of {3-[(9-ethyl-9H-carbazol-3-ylcarbamoyl)-methyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-carbamic acid tert-butyl ester (4.6 mmol) in 1:1 4 M HCl/dioxane (25 mL) was stirred at room temperature for 16 hours. The reaction mixture was then concentrated, and the residue was concentrated from diethyl ether (2×25 mL). The pale yellow foam remaining (723 mg, 37%) was N-(9-ethyl-9H-carbazol-3-yl)-2-(6-amino-3-aza-bicyclo[3.1.0]hex-3-yl)-acetamide.

Provenance & Evidence