Sodium Hydroxide → 3-methoxy-N-{1-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)methyl]piperidin-4-yl}benzamide

Step R1-5: To a suspension of 2-oxo-1,2,3,4-tetrahydroquinoline-7-carbaldehyde (135 g) in CHCl3 (1.4 L) were added 3-methoxy-N-(piperidin-4-yl)benzamide (190 g) and AcOH (45 mL) at room temperature. The mixture was stirred at room temperature for 2 hours. After cooling to 0° C., NaBH(OAc)3 was added portionwise. The mixture was stirred at room temperature for 19 hours. After cooling to 0° C., 8 M aqueous NaOH (0.5 L) and water (0.5 L) were added to the reaction mixture. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated to obtain a colorless solid. The solid was suspended in EtOAc (3.0 L) and the mixture was refluxed for 1 hour and cooled to room temperature. The precipitate was filtrated to obtain a colorless solid. The solid was suspended again in EtOAc (2.4 L), and the mixture was refluxed for 1 hour and cooled to room temperature. The precipitate was filtrated to obtain the titled compound as a colorless solid (229 g).

1. temperatureAfter cooling to 0° C.
2. stirringThe mixture was stirred at room temperature for 19 hours
3. temperatureAfter cooling to 0° C.
4. customThe organic layer was separated
5. washwashed with water and brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customto obtain a colorless solid
9. temperaturethe mixture was refluxed for 1 hour
10. temperaturecooled to room temperature
11. filtrationThe precipitate was filtrated
12. customto obtain a colorless solid
13. temperaturethe mixture was refluxed for 1 hour
14. temperaturecooled to room temperature
15. filtrationThe precipitate was filtrated

ORD 기록

ord-86ff23cddb8f449d8ed8003138a10d37

출처 데이터셋

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08461182B2