Sodium Carbonate → HCID 15712539, compound

Participants

Reaction Steps

A stirred mixture of 1.6 g of 1-benzylpiperazine, 2.9 g of 1-(chloroacetyl)-1,2-dihydro-4-[3-(trifluoromethyl)phenyl]imidazo[1,5-a]pyrimidine-8-carbonitrile and 1.1 g of sodium carbonate in 55 ml of toluene was heated at reflux for 18 hours. The reaction mixture was cooled, then shaken with 20 ml of 1N sodium hydroxide. The layers were separated and the aqueous phase was extracted once with chloroform. The toluene phase above, and the chloroform extract were combined and washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated to obtain a viscous oil. The oil was dissolved in 50 ml of chloroform and passed through hydrous magnesium silicate. The chloroform filtrate was concentrated to an oil. The oil was heated to solution in 25 ml of ethyl acetate and filtered. Then 25 ml of n-hexane was added to the filtrate to crystallize the product. The crystals were collected by filtration, pressed to remove solvent, washed with hexane and dried to give 3.4 g of the product of the example as cream colored crystals, mp 167°-169° C.

Provenance & Evidence