Triethylamine → HCID 86751343, compound

Participants

Reaction Steps

To a stirred mixture of trans-3-(3-pyridyl)acrylic acid (100 mg) and triethylamine (0.19 ml) in dichloromethane (10 ml) was added 1-naphthoyl chloride (0.1 ml) at -15° C. After stirring for 30 minutes, a solution of (2S)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine (300 mg) in dichloromethane (10 ml) was added at -15° C. and the resulting mixture was stirred for 30 minutes at the same temperature and then for 1 hour at room temperature. Dichloromethane and water were added to the reaction mixture and the organic layer was separated, washed successively with aqueous saturated sodium bicarbonate solution, water, 0.5N hydrochloric acid and brine, and dried over magnesium sulfate. After evaporation of the solvent in vacuo, the residue was purified on a silica gel column (20 g) eluting with a mixture of dichloromethane and methanol (100:2) to give (2S)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethyl benzyl)-4-[3-(3-pyridyl)-trans-acryloyl]piperazine (0.34 g).

Provenance & Evidence