3-Bromo-4,5-dimethoxybenzaldehyde → HCID 24955180, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-bromo-4,5-dimethoxybenzaldehyde 111 (5.0 g, 0.020 mol, Aldrich), (R)-1-phenylethanamine (2.6 mL, 0.020 mol, Aldrich) and ACQH (5.0 mL) in 70 mL of MeOH was stirred at room temp. for 2 hours. The solution was then cooled to 0° C. and NaBH3CN solid was added in portions. The reaction solution was then warmed up to room temp and continued to stir overnight. The mixture was concentrated in vacuo and re-dissolved in 150 mL of EtOAc. The organic solution was washed with 50 mL of saturated. NaHCO3 followed by 50 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was passed through a short silica gel pad (eluted with 50% EtOAc/hex). The eluant was concentrated in vacuo to give a light yellow oil, which solidified upon standing to give desired product (R)—N-(3-bromo-4,5-dimethoxybenzyl)-1-phenylethanamine 112 as white waxy solid (5.1 g, 73%). MS (ESI, pos. ion) m/z: 350.2 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 7.4-7.5 (m, 5H); 6.9 (s, 1H); 7.0 (s, 1H), 3.9 (s, 3H); 3.8 (s, 3H); 3.7-3.9 (m, 3H); 1.7 (d, J=7.0 Hz, 3H).

Provenance & Evidence