Reacción #2122489

Ecuación de reacción

Methanesulfonic acid 1-methoxy-piperidin-4-yl ester

sodium cyanide

sodium bicarbonate

water

→

1-methoxy-piperidine-4-carbonitrile

Rendimiento 86.6%

Disolventes

dimethylsulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThen the mixture was cooled to room temperature
2. 2
   Extracciónextracted three times with diethyl ether
3. 3
   SecadoThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Otrothe solvent evaporated
5. 5
   OtroThe residue was purified by chromatography on silica gel with ethyl acetate/cyclohexane (1:1

Procedimiento

200 mg Methanesulfonic acid 1-methoxy-piperidin-4-yl ester (from Step 2), 251 mg tetrabutylammonium cyanide and 272 mg sodium cyanide were mixed in 1 ml dimethylsulfoxide, and heated to 55° C. for 18 hours. Then the mixture was cooled to room temperature, 1 ml saturated aqueous sodium bicarbonate and 3 ml water were added, and extracted three times with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and the solvent evaporated. The residue was purified by chromatography on silica gel with ethyl acetate/cyclohexane (1:1, then 2:1, then pure ethyl acetate) as a solvent. 116 mg 1-methoxy-piperidine-4-carbonitrile was obtained.

Fuente