[Synthesis]
General procedure for the synthesis of 1-(2-hydroxyethyl)piperidine-4-carbonitrile from 4-cyanopiperidine and 2-bromoethanol: 2-bromoethanol (1.36 g, 11 mmol) and piperidine-4-carbonitrile (1.0 g, 9.1 mmol) were dissolved in 5 mL of dimethylformamide. Subsequently, 4.0 g of anhydrous sodium carbonate and 0.08 g of sodium iodide were added to the resulting solution and the mixture was stirred at 130 °C for 4 hours. Upon completion of the reaction, the mixture was poured into ice water and extracted with ethyl acetate. The organic phase was purified by silica gel column chromatography to afford 1-(2-hydroxyethyl)piperidine-4-carbonitrile (300 mg, 18% yield).1H-NMR (CDCl3, 400 MHz): δ 3.58 (t, J = 4.6 Hz, 2H), 2.60-2.75 (m, 4H), 2.50-2.60 (m, 2H), 2.31-2.46 (m, 2H). 2H), 1.70-2.00 (m, 4H). |