[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH2:8]Br)=[CH:4][CH:3]=1.[CH3:12][NH:13][CH2:14][CH2:15][C:16]#[N:17]>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.[OH-].[Na+]>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH2:8][N:13]([CH3:12])[CH2:14][CH2:15][C:16]#[N:17])=[CH:4][CH:3]=1
A solution of 116 g of p-chlorocinnamyl bromide in 500 ml of methylene chloride is added dropwise with stirring to a mixture of 42 g of 3-methylamino-propionitrile and 8.9 g of benzyl-tri-(n-butyl)ammonium bromide in 1 liter of methylene chloride and 500 ml of 2 N sodium hydroxide solution at room temperature and under a nitrogen atmosphere, and the emulsion stirred for 65 hours at room temperature. The organic phase is separated, washed with water, dried over sodium sulphate and evaporated to yield 3-[N-(p-chlorocinnamyl)-methylamino]-propionitrile. M.P. 143° [hydrogen oxalate form]
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