4-Bromobenzoyl chloride → 4-bromo-N-(3-cyclopentylpropyl)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a cold (0° C.) solution of 7-[(3-cyclopentylpropyl)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one (1.70 g, 5.60 mmol) in pyridine (10 mL) was added 4-bromobenzoyl-chloride (Aldrich, 1.47 g, 6.72 mmol) and the resulting reaction mixture was stirred 10 min at 0° C., 30 min at rt and 7 hrs at 60° C. The solvent was removed under reduced pressure. Purification by flash chromatography on silicagel (EtOAc/c-Hex (15/85)) gave 1.6 g (59%) of the title compound as a white solid. HPLC, Rt: 5.2 min (purity: 99.5%). 1H NMR (CDCl3) δ: 7.81 (d, J=7.3 Hz, 1H), 7.35 (d, J=8.7 Hz, 2H), 7.18 (d, J=8.7 Hz, 2H), 6.76 (dd, J=1.9 Hz, J=8.3 Hz, 1H), 6.56 (d, J=1.9 Hz, 1H), 3.91 (t, J=7.9 Hz, 2H), 1.80-1.25 (m, 17H), 1.12-0.95 (m, 2H).

Provenance & Evidence