Pyridine → 4-(4-Fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxycarbonyl]-piperidine-6-one

Temperature

60 °C

A solution of 4-(4-fluorophenyl)-3-carboxyethylpiperidin-6-one (0.5 g, 1.88 mmol, trans/cis ratio 56:44) in ethanol (10 ml) was added to a solution of sodium hydroxide (0.08 g, 2 mmol) in 95% ethanol (5 ml) and the mixture heated for 4 hours at 60° C. The solvent was removed at reduced pressure and the residue of water removed by distillation with toluene. The residue was suspended in dichloromethane (5 ml), treated with a solution of thionyl chloride (0.24 g, 2 mmol), and the mixture was brought to reflux. After 1 hour evolution of sulphur dioxide ceased, so the mixture was cooled to room temperature and treated with pyridine (0.16 g, 2 mmol) followed by a solution of sesamol (0.24 g, 1.75 mmol) in chloroform (2.5 ml). The resulting mixture was brought to reflux, heated for 4 hours, and stirred at ambient temperature for 2 days. The solvent was then removed at reduced pressure and the residue treated with water (5 ml), then extracted with ethyl acetate (20 and 10 ml). The organic extracts were combined, washed with brine (20 ml), dried over anhydrous sodium sulphate, filtered and evaporated to give the title compound (0.32 g).

1. customThe solvent was removed at reduced pressure
2. customthe residue of water removed by distillation with toluene
3. temperatureto reflux
4. temperaturewas cooled to room temperature
5. temperatureto reflux
6. temperatureheated for 4 hours
7. customThe solvent was then removed at reduced pressure
8. additionthe residue treated with water (5 ml)
9. extractionextracted with ethyl acetate (20 and 10 ml)
10. washwashed with brine (20 ml)
11. dry with materialdried over anhydrous sodium sulphate
12. filtrationfiltered
13. customevaporated

ORD record

ord-df002cd9bb3f4fbfa3e6d24fdf45cf93

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06489347B1