Hydrochloric Acid → 1,2,3,4,8,9,10,11,12,13-Decahydrocycloocta[b][1,4]diazepino[6,7,1-hi]indole

Participants

Reaction Conditions

Reaction Steps

3-Acetyl-1,2,3,4,8,9,10,11,12,13-decahydrocycloocta[b][1,4]diazepino[6,7,1-hi]indole (1.3 g) was dissolved in methanol and diluted with 2.5N NaOH and excess solid NaOH was added. The solution was heated at 95° C. overnight. The volatiles were evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic phase was separated and evaporated and the residue was purified by chromatography on silica gel eluting with 3-4% methanol in methylene chloride to give a colorless oil. The oil was treated with 4 N HCl with stirring and warming. The precipitate that formed was isolated by filtration, triturated with ethanol, and allowed to stand overnight. A yellow solid was isolated by filtration and dried to give the hydrochloride salt of the title compound (683 mg), mp: 316-318° C.

Provenance & Evidence