Benzoyl chloride → HCID 22129672, compound

Participants

Reaction Conditions

Reaction Steps

Benzoyl chloride (290 mg) and triethylamine (420 mg) were added to a solution of 2-(3,4-Dichlorophenyl)-2-(4-hydroxy-4-phenylpiperdino)ethylamine (750 mg) in tetrahydrofuran (37.5 mL). The reaction was stirred at 23° C. for 18 hours, and was evaporated to an oil-solid mixture. The mixture was partitioned between water (100 mL) and dichloromethane (100 mL), and the seperated organic layer was dried and evaporated to an off-white solid (1.01 gm). Treatment of a solution of this solid in diethylether with hydrochloric acid (g)/diethylether followed by recrystalization of the hydrochloride salt from ethylacetate (hot,minimum volume) provided the title compound as a white solid (450 mg); mp 232°-235° C.; MS: m/z=469(M+1); NMR: 1.8 (m, 2), 2.44 (m, 1), 2.63 (m, 1), 3.17 (m,3), 3.99 (m,2), 4.27 (m,1), 4.76 (m, 1), 5.4 (broad s,1), 7.26 (m,1), 7.46 (m,7), 7.8 (m, 5), 11.37 (broad s,1). Analysis Calculated: C, 61.73; H, 5.38; N, 5.54; Found: C, 61.8; H, 5.5; N, 5.52.

Provenance & Evidence