Hydrochloric Acid → 1-Nitrosopiperidine-3-carboxylic acid

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.

1. temperatureThe mixture was cooled with an ice bath
2. extractionThe mixture was extracted with dichloromethane (20 mL×3)
3. washThe combined organics were washed with brine (2×), solids
4. customwere removed by filtration
5. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-8ee4bb0e323c454ca1d25f580d74ac1f

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296745B2