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• Synthesis

  A round bottom flask was charged with oxalyl chloride (16.2 g, 0.12 mol), dichloromethane (150 mL) and anhydrous dimethyl sulfoxide (20 mL). Stir the reaction mixture mass in a cryo bath at -70 °C for 15 min. The resulting mixture is charged dropwise with N-benzyl piperidine alcohol 3 (20 g, 0.097 mol), along with triethylamine (24.6 g, 0.24 mol) and continued stirring for the next 15 min. After that, the mass is allowed to attain room temperature overnight, then diluted with dichloromethane (100 mL) and quenched with cold water. The organic layer was washed subsequently with 5 % HCl solution, brine solution, 5 % sodium bicarbonate solution and dried over sodium sulfate. Toluene was removed in vacuo to afford N-Benzylpiperidine-4-carboxaldehyde (19.2 g, 96 %).
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