2-Bromopropiophenone → 2-{[4-(2-Hydroxyethyl)phenyl]amino}-1-phenyl-1-propanone

Participants

Reaction Steps

A mixture of 4-aminophenethyl alcohol (690 mg, 5.0 mmol), 2-bromopropiophenone (2.1 g, 10 mmol) potassium carbonate (690 mg, 5.0 mmol) in DMF (50 mL) was stirred at ambient temperature for 3 days. The mixture was partitioned between ethyl acetate and water. The combined organic phase was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (2:1) to afford the title compound quantitatively as yellow oil: 1H-NMR (CDCl3) δ 1.49 (2H, d, J=6.9 Hz), 2.74 (2H, t, J=6.4 Hz), 3.79 (2H, t, J=6.4 Hz), 4.65 (1H, br), 5.11 (1H, m), 6.65 (2H, d, J=8.4 Hz), 7.05 (2H, d, J=8.6 Hz), 7.48-7.65 (3H, m), 8.03 (2H, d, J=7.2 Hz).

Provenance & Evidence