4-Methoxybenzenesulfonyl chloride → 2-[(N,N-Dimethylamino)methyl]-6-[4-[(4-methoxyphenyl) sulfonylamino)benzyloxy]tetralin

Participants

Reaction Steps

THF solution (1 ml) of 4-methoxybenzenesulfonyl chloride (270 mg) was added dropwise to pyridine solution (6 ml) of 6-[(4-aminobenzyl)oxy]-2-[(N,N-dimethylamino)methyl]tetralin (300 mg) under ice-cooling, which was stirred for 15 minutes. After stirring at room temperature for further 15 minutes, 10% aqueous potassium carbonate solution was added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using alumina column chromatography (development solvent: ethyl acetate), and recrystallized (ethyl acetate-IPE) to give the titled compound (260 mg).

Provenance & Evidence