[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]#[N:9].Cl.[CH2:11]([N:18]([CH2:22][CH2:23]Cl)[CH2:19][CH2:20]Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC>[CH2:11]([N:18]1[CH2:22][CH2:23][C:7]([C:8]#[N:9])([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Combine 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.
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