Triethylamine → HCID 54276261, compound

Participants

Reaction Steps

To a solution of 3,5-bis(trifluoromethyl)benzoic acid (2.63 g) and (5R)-5-(1H-indol-3-ylmethyl)piperazin-2-one (2.34 g) in dichloromethane (50 ml) were added successively triethylamine (3.56 ml) and 2-chloro-1-methylpyridinium iodide (3.13 g) at room temperature. The resulting mixture was stirred for 1.5 hours at the same temperature. Dichloromethane and water were added into the mixture and the organic layer was separated. The organic layer was washed successively with 0.5N hydrochloric acid, water, aqueous sodium bicarbonate solution and brine, and dried over magnesium sulfate. After evaporation in vacuo, the residue was purified by column chromatography on silica gel (75 g) eluting with a mixture of dichloromethane-methanol (from 0% to 5% gradient elution) to give (5R)-4-[3,5-bis(trifluoromethyl)benzoyl]-5-(1H-indol-3-ylmethyl)piperazin-2-one (1.25 g) as an oil.

Provenance & Evidence