Benzyl Bromide → 1-Benzyl-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine

Benzyl bromide (52.4 mL, 441 mmol) was added to a solution of 4-(4-fluorophenyl)pyridine (Description 14, 50.87 g, 294 mmol) in acetone (500 mL) and the mixture was heated under reflux for 3 days. The mixture was cooled to room temperature and the solid was collected, washed with acetone and diethyl ether and dried in vacuo. The solid was dissolved in methanol (400 mL) and water (100 mL), cooled to 0° C. and sodium borohydride (20.6 g, 542 mmol) was added in portions. The mixture was stirred at room temperature for 1 hour, then heated to reflux for 18 hours. The mixture was cooled and the solvent was evaporated under reduced pressure. Dichloromethane (300 mL) and water (200 mL) were added and the layers were separated. The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a light brown oil (61.5 g, 78%). m/z (ES+) 268 (M+1).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 3 days
3. customthe solid was collected
4. washwashed with acetone and diethyl ether
5. customdried in vacuo
6. dissolutionThe solid was dissolved in methanol (400 mL)
7. temperaturewater (100 mL), cooled to 0° C.
8. temperatureheated
9. temperatureto reflux for 18 hours
10. temperatureThe mixture was cooled
11. customthe solvent was evaporated under reduced pressure
12. additionDichloromethane (300 mL) and water (200 mL) were added
13. customthe layers were separated
14. dry with materialThe organic layer was dried (MgSO4)
15. customthe solvent was evaporated under reduced pressure

ORD record

ord-7ab6881b6326435088c982c926dd085b

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06953792B2