Dichloromethane → HCID 86751325, compound

Participants

Reaction Steps

To a stirred solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (400 mg) in dichloromethane (5 ml) was added 1,1'-carbonyldiimidazole (140 mg) at room temperature. The resulting mixture was stirred overnight. Additional 1,1'-carbonyldiimidazole (70 mg) was added to the mixture and then stirred for 1 hour. After the dichloromethane was removed under reduced pressure, N-methylpropylamine (1 g) was added. The mixture was stirred at room temperature for 2 hours and then at reflux temperature for 12 hours. After cooling, dichloromethane and water were added to the reaction mixture. The organic layer was separated, washed with aqueous 0.5N hydrochloric acid and brine. After evaporation of the solvent, the residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (99:1) to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)-4-(N-methyl-N-propylcarbamoyl)piperazine (0.18 g).

Provenance & Evidence