Hydrochloric Acid → 1-Nitrosopiperidine-3-carboxylic acid

Participants

Reaction Steps

Aqueous hydrochloric acid (2N, 20 mL) was added to piperidine-3-carboxylic acid (5.02 g, 38.87 mmol). The mixture was cooled with an ice bath and a solution of sodium nitrite (2.78 g, 40.29 mmol) in water (4 mL) was added. The reaction mixture was stirred at room temperature for 15 h. The mixture was extracted with dichloromethane (20 mL×3). The combined organics were washed with brine (2×), solids were removed by filtration and the filtrate was concentrated under reduced pressure to afford 1-nitrosopiperidine-3-carboxylic acid (4.5 g). MS (EI+) (M+) 158.

Provenance & Evidence