4-Toluenesulfonyl chloride → HCID 13749135, compound

Participants

Reaction Steps

To a solution of 6,7,8,9-tetrahydro-10-methylpyrido[1,2-a]indol-9-ol (2.01 g, 10 mmol) in dry pyridine (100 mL) was added a solution of p-toluenesulfonyl chloride (7.6 g, 10 mmol) in the same solvent (50 mL) at 5°-10° C. Maintaining this temperature, stirring was continued for 60 minutes, and then, the reaction mixture was treated with distilled pyrrolidine (7.1 g, 100 mmol), and stirred at room temperature for 8 hours. The resultant solution was poured into ice-water, and the product was extracted with methylene chloride. The combined extracts were washed with water, dried (MgSO4), filtered, and evaporated. The residue was chromatographed using methylene chloride/methanol 99:1. The title base 1.8 g (70%) was converted to the hydrochloride salt in acetonitrile with ethereal HCl, and recrystallized from ethanol, m.p. 179°-181° C. (analytical specimen m.p. 182° C.).

Provenance & Evidence