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

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Reaction Steps

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.

Provenance & Evidence