Ethylene Glycol → 10-[2-(Trifluoromethoxy)phenyl]-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

Participants

Reaction Conditions

Reaction Steps

3-Benzoyl-10-[2-(trifluoromethoxy)phenyl]-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (1.55 g, 3.44 mmol) and ethylene glycol (50 mL) were combined and heated to 170° C. KOH (3.91 g, 69.7 mmol) was added and the reaction mixture was stirred at 170° C. for 1.5 h. The reaction mixture was cooled to rt and was combined with EtOAc (100 mL) and H2O (300 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to give crude product (5.22 g). The crude product was chromatographed (SiO2 100 g, eluted with 90:10:1 CH2Cl2:CH3OH:conc. NH4OH) to give 10-[2-(trifluoromethoxy)phenyl]-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.82 g) in 69% yield. 1H NMR (400 MHz, CD3OD) δ 2.24-2.36, 2.70-2.76, 2.95-3.03, 6.75, 7.06, 7.30, 7.36-7.42, 7.46-7.51; MS (ESI+) for C19H17F3N2O m/z 347.2 (M+H)+.

Provenance & Evidence