4-amino-N-methylpiperidine-1-sulfonamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Triethylamine (1.5 mL) was added to a dichloromethane (30 mL) solution of Benzyl piperidin-4-ylcarbamate (580 mg) at 0° C. followed by the dropwise addition of chlorosulfonic acid (290 μL; TCI), the resulting mixture was stirred at room temperature for 4 hours, and the solvent was evaporated under reduced pressure. Benzene (32 mL) and phosphorus pentachloride (0.7 g; WAKO) were added to this residue and the resulting mixture was stirred at 80° C. for 1.5 hours. The reaction mixture solution was cooled to room temperature followed by the addition of 1 N aqueous sodium hydroxide solution (10 mL), the resulting mixture was extracted with dichloromethane, the organic layer was dried, then the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Yamazen; hexane/ethyl acetate). 30 mg of this purified compound was dissolved in dichloromethane (0.4 mL) followed by the addition of 3,5-lutidine (0.4 mL; WAKO) and methylamine (2 M, 70 μL; Ald) and the resulting mixture was stirred at room temperature for 24 hours. 1 N hydrochloric acid (2 mL; WAKO) was added to the reaction mixture solution, the resulting mixture was stirred for approx. 10 minutes, then the reaction mixture was extracted with dichloromethane, the organic layer was dried, and then the solvent was evaporated under reduced pressure. The title compound was obtained from this residue according to the method described in Step c of Reference Example N-14. the solvent was evaporated under reduced pressure Benzene (32 mL) and phosphorus pentachloride (0.7 g; WAKO) were added to this residue the resulting mixture was stirred at 80° C. for 1.5 hours The reaction mixture solution was cooled to room temperature followed by the addition of 1 N aqueous sodium hydroxide solution (10 mL) the resulting mixture was extracted with dichloromethane the organic layer was dried the solvent was evaporated under reduced pressure the residue was purified by silica gel column chromatography (Yamazen; hexane/ethyl acetate) 30 mg of this purified compound was dissolved in dichloromethane (0.4 mL) followed by the addition of 3,5-lutidine (0.4 mL; WAKO) and methylamine (2 M, 70 μL; Ald) the resulting mixture was stirred at room temperature for 24 hours 1 N hydrochloric acid (2 mL; WAKO) was added to the reaction mixture solution the resulting mixture was stirred for approx. 10 minutes the reaction mixture was extracted with dichloromethane the organic layer was dried the solvent was evaporated under reduced pressure