Sodium Carbonate → HCID 57430015, compound

Participants

Reaction Steps

{[4-(3-Bromopyridin-2-yl)-1-(propylsulfonyl)piperidin-4-yl]methyl}amine hydrochloride salt (100 mg, 0.24 mmol) was dissolved in dichloromethane (5 mL) with N,N-diisopropylethylamine (0.13 mL, 0.72 mmol). 2,4-dichlorobenzoyl chloride (34 μL, 0.24 mmol) was added and the mixture stirred over night. The mixture was poured into aqueous sodium carbonate (10 mL, 2 M) and extracted with dichloromethane (10 mL x 2). The combined organic phases were dried over magnesium sulphate (anhydrous), filtered and evaporated. The reside was purified by flash column chromatography on silica gel using dichloromethane containing 10% ethyl acetate as eluent to afford the desired product: N-{[4-(3-bromopyridin-2-yl)-1-(propylsulfonyl)piperidin-4-yl]methyl}-2,4-dichlorobenzamide: 1H NMR δ (ppm)(CDCl3): 8.50 (1 H, dd, J=1.4, 4.5 Hz), 7.94 (1 H, dd, J=1.4, 7.9 Hz), 7.58 (1 H, d, J=8.3 Hz), 7.36(1 H, d, J=1.9 Hz), 7.29 (1 H, dd, J=8.3, 1.9 Hz), 7.10 (1 H, dd, J=4.5, 7.9 Hz), 6.87 (1 H, m), 5.30 (1 H, s), 4.15 (2 H, d, J=6.2 Hz), 3.46-3.44 (4 H, m), 3.14-3.08 (2 H, m), 2.90-2.88 (2 H, m), 1.90-1.76 (4 H, m), 1.06 (3 H, t, J=7.4 Hz); m/z (ES) 548, 550 (M+H).

Provenance & Evidence