N-[(3,4-dimethoxyphenyl)methyl]-1-phenylmethanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of benzylamine (3.94 mL, 36 mmol) and 4,3-dimethoxybenzaldehyde (5.0 g, 30 mmol) in chloroform (120 mL), was added sodium triacetoxyborohydride (9.53 g, 45 mmol). The mixture was stirred at rt for 18 hrs prior to addition of saturated NaHCO3. The organic phase was separated and the aqueous phase extracted with chloroform. The combined extracts were washed with brine, dried over MgSO4 and evaporated to afford the crude product. Purification by flash column chromatography afforded the title compound as a pale yellow oil (5.47 g, 71%). 1H NMR (270 MHz, CDCl3) δ 3.74 (2H, s), 3.80 (2H, s), 3.86 (3H, s), 3.88 (3H, s), 6.80-6.89 (3H, m), 7.22-7.34 (5H, m); HRMS (ESI+) calcd. for C16H20NO2 (M++H) 258.1489, found 258.1478; LC/MS (ES+) tr=0.79 min, m/z 258.2 (M++H). The organic phase was separated the aqueous phase extracted with chloroform The combined extracts were washed with brine dried over MgSO4 evaporated to afford the crude product Purification by flash column chromatography