Sodium Hydroxide → 935259-98-6

To a solution of 4,4-difluoropiperidin hydrochloride (2.0 g) in water was added 2N sodium hydroxide (7.6 mL) and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added sodium nitrite (1.75 g) at room temperature and added acetic acid (1.27 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added an aqueous sodium hydrogencarbonate solution and the mixture was extracted with chloroform. The extract was dried over magnesium sulfate and filtered, and the filtrate was concentrated in vacuo. The resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=4/1) to give 4,4-difluoro-1-nitrosopiperidine (1.89 g, yield: 99%) as a pale yellow solid.

1. temperaturecooling
2. stirringthe mixture was stirred at room temperature for 2 hours
3. extractionthe mixture was extracted with chloroform
4. dry with materialThe extract was dried over magnesium sulfate
5. filtrationfiltered
6. concentrationthe filtrate was concentrated in vacuo
7. customThe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=4/1)

ORD record

ord-4f47eea18f8340fd97b6583f56c7891c

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188097B2