Dibutylamine → HCID 53697728, 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 1.0 ml (6.0 mmol) of dibutylamine and stirred at room temperature under argon for 3 hrs. The solution was evaporated, the residue was triturated in 10 ml of water and the crystals were filtered off under suction. The crude product was dissolved in methylene chloride, the solution was dried with sodium sulfate, whereupon it was chromatographed on 30 g of silica gel (methylene chloride/acetone 9:1, then 4:1). There was obtained 0.73 g of (S)-1-(5-dibutylaminomethyl-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 in 10 ml of acetonitrile with ethereal hydrochloric acid into the hydrochloride. By crystallization from hot ethyl acetate there was obtained 0.75 g (77%) of (S)-1-(5-dibutylaminomethyl-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) of m.p. 115°-123° (dec.).

Provenance & Evidence