4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-ethyl ester

Participants

Reaction Steps

To a cooled (0° C.) solution of of 2-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-ethanol (425 mg, 1.56 mmol) in dichloromethane (20 mL) was added triethylamine (0.9 mL, 6.49 mmol) and tosyl chloride (1115 mg, 5.85 mmol). The reaction mixture was stirred 22 h at room temperature. An aqueous solution of NaHCO3 was added. After separation, the organic layer was washed with brine. The brown gum was triturated with diethylether. After filtration, the solid was dried in a high vacuum to give 520 mg (78.1%) of toluene-4-sulfonic acid 2-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-ethyl ester as a light yellow solid. ISP mass spectrum, m/e: 427.5 (M+1 calculated for C23H26N2O4S: 427.5).

Provenance & Evidence