Water → HCID 69894756, compound

Participants

Reaction Conditions

Reaction Steps

In a 50 mL 2-neck round-bottomed flask 10-(3,5-difluorophenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole hydrochloride was dissolved in TFA (3 mL) and cooled to 0° C. A solution of sodium cyanoborohydride (0.084 g, 1.34 mmol) in MeOH was added and the mixture was stirred at room temperature for 2 h. Water was added, followed by 15% NaOH until the pH of the mixture was basic, and the mixture was extracted with EtOAc. The organic layer was concentrated to give 0.21 g of a brown oil. Column chromatography (elution with 2-6% MeOH/chloroform) gave 0.060 g (74%) of the title product as a clear oil: MS (EI) m/z 300 (M+), 300, 256, 255, 244, 243, 242, 240, 229, 201, 56; HRMS (FAB) calcd for C18H18F2N2+H1 301.1516, found 301.1500.

Provenance & Evidence