Triethylamine → HCID 67402894, compound

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.

1. customthe solvent was evaporated under reduced pressure
2. additionBenzene (32 mL) and phosphorus pentachloride (0.7 g; WAKO) were added to this residue
3. stirringthe resulting mixture was stirred at 80° C. for 1.5 hours
4. temperatureThe reaction mixture solution was cooled to room temperature
5. additionfollowed by the addition of 1 N aqueous sodium hydroxide solution (10 mL)
6. extractionthe resulting mixture was extracted with dichloromethane
7. customthe organic layer was dried
8. customthe solvent was evaporated under reduced pressure
9. customthe residue was purified by silica gel column chromatography (Yamazen; hexane/ethyl acetate)
10. dissolution30 mg of this purified compound was dissolved in dichloromethane (0.4 mL)
11. additionfollowed by the addition of 3,5-lutidine (0.4 mL; WAKO) and methylamine (2 M, 70 μL; Ald)
12. stirringthe resulting mixture was stirred at room temperature for 24 hours
13. addition1 N hydrochloric acid (2 mL; WAKO) was added to the reaction mixture solution
14. stirringthe resulting mixture was stirred for approx. 10 minutes
15. extractionthe reaction mixture was extracted with dichloromethane
16. customthe organic layer was dried
17. customthe solvent was evaporated under reduced pressure

ORD record

ord-7a1b5701d56b499c987d72497ba77d62

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299055B2