Reacción #340243

Ecuación de reacción

sodium hydrogencarbonate

sodium nitrite

4,4-difluoropiperidine hydrochloride

sodium hydroxide

→

4,4-difluoro-1-nitrosopiperidine

Rendimiento 99.2%

Disolventes

acetic acid

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for 2 hours
3. 3
   workup.STIRRINGthe mixture was stirred
4. 4
   Extracciónextracted with chloroform
5. 5
   SecadoThe extract was dried over magnesium sulfate
6. 6
   Filtraciónfiltered
7. 7
   ConcentraciónThe filtrate was concentrated in vacuo
8. 8
   Otrothe resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=4/1)

Procedimiento

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.

Fuente