Potassium Carbonate → 2-(1-Benzylpiperidin-4-ylidene)acetonitrile

A mixture of diethyl cyanomethylphosphonate (2.06 g, 11.62 mmol) and anhydrous potassium carbonate (1.6 g, 11.62 mmol) in dry THF (10 mL) was stirred at room temperature for 15 min and then refluxed for 20 min. After cooling to room temperature, benzyl-piperidin-4-one (compound of Example 25; 2 g, 10.56 mmol) was added and the mixture was heated at reflux for 16 h (˜70° C.). The reaction mixture was cooled to room temperature, filtered and quenched with ice water (25 mL). The resulting mixture was extracted with ethyl acetate (2×20 mL) and the combined organic layers were washed with water (2×15 mL) followed by brine (20 mL). The organic phase obtained was dried over anhydrous sodium sulphate and concentrated to obtain a crude product, which was purified by crystallisation using 2% ethyl acetate in hexane to afford the title compound.

1. temperaturerefluxed for 20 min
2. temperatureAfter cooling to room temperature
3. temperaturethe mixture was heated
4. temperatureat reflux for 16 h (˜70° C.)
5. temperatureThe reaction mixture was cooled to room temperature
6. filtrationfiltered
7. customquenched with ice water (25 mL)
8. extractionThe resulting mixture was extracted with ethyl acetate (2×20 mL)
9. washthe combined organic layers were washed with water (2×15 mL)
10. customThe organic phase obtained
11. dry with materialwas dried over anhydrous sodium sulphate
12. concentrationconcentrated
13. customto obtain a crude product, which
14. customwas purified by crystallisation

ORD record

ord-9b599b2837f143f184907747373190c5

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629277B2