Sodium Carbonate → 5-Bromo-2-(2-ethylpiperidin-1-YL)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-fluorobenzaldehyde (20 g, 0.099 mol) in dimethyl sulfoxide (230 mL) and water (70 mL), were added 2-ethylpiperidine (14.4 mL, 0.1083 mol) and sodium carbonate (20.88 g, 0.197 mol). The resulting mixture was heated at 110° C. for a period of 30 h. The reaction mixture was cooled to room temperature, diluted with water (1000 mL), extracted by methyl tert-butyl ether (2×500 mL), dried using sodium sulphate and concentrated under reduced pressure. The resulting crude was purified by column chromatography on silica gel (60-120 mesh) using pet ether as eluent to afford the titled compound as a yellow liquid. 1H NMR (DMSO-d6, 400 MHz) δ 10.15 (1H, s), 7.70-7.73 (2H, d), 7.22-7.25 (1H, m), 3.08-3.13 (2H, m), 2.84-2.86 (1H, m), 1.83-1.84 (1H, m), 1.34-1.67 (7H, m), 0.62-0.66 (3H, t).

Provenance & Evidence