Reacción #487243

Ecuación de reacción

4-pyridylacetonitrile

N-benzyl-N,N-bis-(2-chloroethyl)amine hydrochloride

hydrochloric acid

dioxane

sodium hydroxide

→

1-benzyl-4-cyano-4-(pyridin-4-yl)-piperidine hydrochloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacool the reaction mixture to ambient temperature
2. 2
   Extracciónrepeatedly extract with diethyl ether
3. 3
   ExtracciónExtract the combined organic layers twice with an aqueous 10% hydrochloric acid solution (350 mL)
4. 4
   ExtracciónAgain extract three times with diethyl ether
5. 5
   Secadodry over MgSO4
6. 6
   Filtraciónfilter
7. 7
   Otroevaporate in vacuo

Procedimiento

Combine 4-pyridylacetonitrile (19.4 g, 125 mmol), N-benzyl-N,N-bis-(2-chloroethyl)amine hydrochloride (33.6 g, 125 mmol), and hexadecyltributylphosphonium bromide (3 g, 6 mmol) and a 50% aqueous sodium hydroxide solution. Heat to 100° C. After 1 hour, cool the reaction mixture to ambient temperature and repeatedly extract with diethyl ether. Extract the combined organic layers twice with an aqueous 10% hydrochloric acid solution (350 mL). Combine the aqueous layers and neutralize with an aqueous 50% sodium hydroxide solution. Again extract three times with diethyl ether, combine the organic layers, dry over MgSO4, and filter. Add a solution of hydrochloric acid in dioxane (60 mL 4M, 240 mmol) and evaporate in vacuo to give 1-benzyl-4-cyano-4-(pyridin-4-yl)-piperidine hydrochloride.

Fuente