Formaldehyde → 4-(Benzyloxy)-1-(2,6-dimethyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)pyridin-2(1H)-one

Participants

Reaction Steps

4-(Benzyloxy)-1-(6-methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)pyridin-2(1H)-one hydrochloride (54 mg, 0.12 mmol) and 37% aqueous formaldehyde (15 μL, 0.17 mmol) were dissolved in 1:1 MeOH/CH2Cl2 (1.0 mL), and the resulting solution was stirred at room temperature for 5 min. Sodium triacetoxyborohydride (52 mg, 0.25 mmol) was added, and the reaction stirred at room temperature for an additional 45 min. The mixture was neutralized with saturated NaHCO3 solution and extracted with CH2Cl2 (2×10 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness. Flash chromatography (12 g ISCO CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 2 column volumes to 0:100 over 20 column volumes) provided the title compound (24 mg, 46%) as a yellow film: 1H NMR (300 MHz, CD3OD) δ 7.60-7.55 (m, 2H), 7.47-7.35 (m, 6H), 7.01-6.98 (m, 1H), 6.29-6.26 (m, 1H), 6.11 (d, J=2.7 Hz, 1H), 5.48 (s, 2H), 5.17 (s, 2H), 4.16-4.10 (m, 2H), 3.74-3.73 (m, 3H), 3.10-3.06 (m, 2H), 2.61 (s, 3H), 2.12-2.06 (m, 2H).

Provenance & Evidence