N-Methylbenzylamine → HCID 86751320, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-(2-chloroacetyl)piperazine (300 mg) in tetrahydrofuran (5 ml) was added N-methylbenzylamine (140 mg) at room temperature. After stirring for 2 hours, additional N-methylbenzylamine (70 mg) was added, and then the whole was heated at 45° C. for 6 hours. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate (20 ml) and aqueous sodium bicarbonate solution (10 ml). The organic layer was separated and dried over magnesium sulfate. After evaporation of the solvent in vacuo, the residue was purified by column chromatography on a silica gel eluting with a mixture of dichloromethane and methanol (50:1) and treated with 4N hydrogen chloride in ethyl acetate solution to afford (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[2-(N-benzyl-N-methylamino)acetyl]-2-(3,4-dimethylbenzyl)piperazine hydrochloride (0.35 g).

Provenance & Evidence