Sodium Hydroxide → 935259-98-6

To a solution of 4,4-difluoropiperidine hydrochloride (2.0 g) in water (32 mL) was added an aqueous 2N sodium hydroxide solution (7.6 mL) and the mixture was stirred at room temperature for 1 hours. To the reaction mixture was added sodium nitrite (1.75 g) and thereto was added acetic acid (1.27 mL) under ice-cooling. 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 stirred and extracted with chloroform. The extract was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=4/1) to obtain 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. stirringthe mixture was stirred
4. extractionextracted with chloroform
5. dry with materialThe extract was dried over magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated in vacuo
8. customthe resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=4/1)

ORD record

ord-365cd7dd2ef4454ead9ecb0cda8a6027

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872006B2