Sodium hydride → HCID 70110276, compound

Participants

Reaction Steps

2-(Chloromethyl)quinoline hydrochloride (321 mg, 1.5 mmol) was dissolved in water (0.5 mL) and ethyl acetate (1 mL), which was neutralized with sodium hydrogencarbonate. The organic layer was separated, and the aqueous layer was subjected to extraction twice with ethyl acetate. The organic layers were combined and dried over magnesium sulfate, which was concentrated under reduced pressure. To the concentrate were added (3aR*,10aS*)-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-one (390 mg, 1.0 mmol) and N,N-dimethylformamide (3 mL). To this suspension was added, at 0° C., sodium hydride (60% liquid paraffin dispersion, 48 mg, 1.2 mmol), and the mixture was stirred for 20 minutes at room temperature. To the reaction mixture was added water, which was subjected to extraction twice with chloroform. Organic layers were combined, washed with water, dried over magnesium sulfate, subjected to filtration and, then, concentrated under reduced pressure. The concentrate was crystallized from ethanol-hexane to give 243 mg (yield 46%) of the titled compound, m.p. 258°-260° C.

Provenance & Evidence