反応 #487249

反応方程式

2-pyridylacetonitrile

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

sodium hydroxide

→

1-benzyl-4-cyano-4-(pyridin-2-yl)-piperidine

反応条件

後処理

1. 1
   温度cool the reaction mixture to ambient temperature
2. 2
   抽出repeatedly extract with diethyl ether
3. 3
   抽出Extract the combined organic layers twice with an aqueous 10% hydrochloric acid solution (350 mL)
4. 4
   抽出Again extract three times with diethyl ether
5. 5
   乾燥dry over MgSO4
6. 6
   ろ過filter
7. 7
   その他evaporate in vacuo

実験手順

Combine 2-pyridylacetonitrile (5.9 g, 50 mmol), N-benzyl-N,N-bis-(2-chloroethyl)amine hydrochloride (13.4 g, 50 mmol), and hexadecyltributyphosphonium bromide (1.3 g, 2.5 mmol) and a 50% aqueous sodium hydroxide solution (75 mL). 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, filter, and evaporate in vacuo to give 1-benzyl-4-cyano-4-(pyridin-2-yl)-piperidine: Rf =0.56 (silica gel, 9/1 dichloromethane/methanol). Elemental Analysis calculated for C18 H19N3 : C, 77.95; H, 6.90; N, 15.15. Found: C, 78.20; H, 6.97; N, 15.04.

出典