Chloroacetyl chloride → (3aR*,10aS*)-9-Benzyl-4-(chloroacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Participants

Reaction Steps

On a water-bath kept at 14° C., to a solution of (3aR*,10aS*)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (5.85 g, 20 mmol) in 1,2-dichloroethane (20 mL) was added dropwise a solution of chloroacetyl chloride (2.5 g, 22 mmol) in 1,2-dichloroethane (15 mL), and the mixture was stirred for 10 minutes. The aqueous layer of this mixture was separated, and the organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, which was subjected to filtration, and the filtrate was concentrated under reduced pressure. The concentrate was recrystallized from dichloromethane-hexane to give 6.49 g (yield 88%) of the titled compound, m.p. 154°-156° C.

Provenance & Evidence