Dipropylamine → HCID 54359519, compound

Participants

Reaction Steps

A solution of 711 mg (2.0 mmol) of (S)-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one in 10 ml of N,N-dimethylformamide was treated with 0.82 ml (6.0 mmol) of dipropylamine and stirred at room temperature under argon for 2 hrs. The solution was evaporated, the residue was triturated in 10 ml of water and the crystals were filtered off. The crude product was chromatographed on 30 g of silica gel (methylene chloride/acetone 9:1, then 4:1). There were obtained 840 mg of (S)-1-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one, which was converted with ethereal hydrochloric acid into the hydrochloride. By recrystallization from acetonitrile there were obtained 685 mg (73%) of (S)-1-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one hydrochloride (1:1.3) of m.p. 137°-140° (dec.).

Provenance & Evidence