Acetonitrile → (+)-N-benzyl-N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}propan-1-amine

Participants

Reaction Steps

N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}propan-1-amine (1.2 g, 4.2 mmol), benzylbromide (0.53 ml, 4.4 mmol), potassium carbonate (0.70 g, 5.0 mmol) and ACN (50 ml) were heated at 60° C. for 2.5 h. EtOAc (100 ml) was added and the mixture was filtered and evaporated to dryness. Purification by flash chromatography (isooctane/EtOAc 1:1) and evaporation of pure fractions afforded the title compound (1.2 g). 1H-NMR (400 MHz, MeOH): δ 7.48 (1H, dd, J1 8.0 Hz, J2 2.0 Hz), δ 7.38-7.21 (7H, m), δ 5.18 (1H, t, J 5.6 Hz), δ 4.97 (2H, dd, J1 41.6 Hz, J2 15.6 Hz), δ 3.77 (2H, q, J 13.6 Hz), δ 3.10 (3H, s), δ 2.94-2.84 (2H, m), δ 2.58 (2H, dt, J1 7.2 Hz, J2 1.6 Hz), δ 1.56 (2H, m), δ 0.90 (2H, t, J 7.2 Hz).

Provenance & Evidence