Acetaldehyde → HCID 21071635, compound

Participants

Reaction Steps

Add acetaldehyde (0.080 mL; 0.77 mmol) to a solution of N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-3-phenyoxybenzylamine (free base, 55.5 mg, 0.149 mmol) in dichloromethane (1 mL) followed by a suspension of sodium triacetoxyborohydride (64 mg; 0.30 mmol) in dichloromethane (1 mL). After 44 hours, quench by the addition of methanol (0.5 mL) and concentrate in a stream of nitrogen to give a residue. Dissolve the residue in 4 mL of 5% acetic acid in methanol and partially purify by passage through a 1 gm SCX column, eluting with 1 M ammonia in methanol to give a residue. Chromatograph the residue by preparative HPLC (C-18 column, flow rate of 20 ml/min, 5–90% water/acetonitrile over 12 min) to give the title compound: MS (ES+): m/e (M+1); HPLC: (10–90% water/acetonitrile over 10 min, Tr=5.25 min).

Provenance & Evidence