Dipropylamine → HCID 22914513, compound

Participants

Reaction Steps

A solution of 370 mg (1.01 mmol) of 8-chloro-3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one in 5 ml of N,N-dimethylformamide was treated with 0.42 ml (3.03 mmol) of dipropylamine and stirred at room temperature under argon for 2 hrs. The solution was evaporated and the residue was triturated in 10 ml of water. The white crystals were filtered off. The product was chromatographed on 20 g of silica gel (ethyl acetate/hexane 1:1, then ethyl acetate). There were obtained 259 mg of 8-chloro-3-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, which was converted with ethereal hydrochloric acid into the hydrochloride. By recrystallization from acetonitrile there were obtained 268 mg (54%) of 8-chloro-1-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one hydrochloride (1:1.6) of m.p. 180°-192° (dec.).

Provenance & Evidence