Pyridine → N-(2,2-Dimethoxyethyl)-N-[(2-fluorophenyl)methyl]-4-methylbenzenesulfonamide

Participants

Reaction Steps

N-(2-fluorobenzyl)-2,2-dimethoxyethanamine (BB; 33.0 g, 0.154 mol) were dissolved in 200 mL of dichloromethane and pyridine (50.2 g, 0.417 mol) was added. At 0° C. a solution of p-toluene sulphonyl chloride (58.0 g, 0.201 mol) in dichloromethane (500 mL) was added drop wise. The reaction was allowed to warm to room temperature and stirring is continued until conversion was completed. For workup, the reaction mixture was extracted twice with 2M aqueous hydrochloric acid, twice with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulphate, evaporated to dryness and the obtained crude product was purified by silica gel chromatography to yield the title compound. 1H NMR (400 MHz, CDCl3) δ 7.69-7.67 (2H, m), 7.43-7.39 (m, 1H), 7.29-7.21 (m, 3H), 7.12-7.08 (m, 1H), 6.99-6.95 (m, 1H), 4.52 (s, 2H), 4.39-4.37 (t, 1H, J=5.2 Hz), 3.26-3.24 (m, 8H), 2.42 (s, 3H).

Provenance & Evidence