Acetic Acid → 1-Nitroso-4-piperidinol

Participants

Reaction Conditions

Reaction Steps

Add a solution of sodium nitrite (13.8 g, 200 mmol) in water (40 mL) to 4-hydroxy piperidine (10.1 g, 100 mmol) in water (20 mL). Cool the mixture to 0° C. on an ice bath. Add acetic acid (8.6 mL, 150 mmol) dropwise over 20 minutes. After the addition, continue stirring at 0° C. for 30 minutes, slowly warm up to room temperature and stir at room temp for 5 hours. Add sodium carbonate (15.9 g, 150 mmol) in portion to quench the acid. Extract the reaction with ethyl acetate (3×60 mL), combine the organic, dry over sodium sulfate, filter and concentrate to afford the desired product as yellow oil. Yield: 12.9 g, (98%).

Provenance & Evidence