[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[CH2:8](Cl)[C:9](=[CH2:11])[CH3:10].C(#N)CCCCC#N.[OH-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]([N:4]([CH2:10][C:9](=[CH2:8])[CH3:11])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2]A mixture of diisopropylamine (20.24 g, 0.2 mol), methallyl chloride (9.00 g, 0.1 mol), adiponitrile (10.81 g, 0.1 mol) and tetrabutylammonium iodide (3.69 g, 10 mmol) was refluxed for 5 h with vigorous stirring (two phases). The temperature of the mixture increased from 88° to 125° C. Potassium hydroxide solution (5M, 15 ml, 0.15 mol) was added. Three layers formed. The mixture was extracted with n-pentane (2×50 ml). Adiponitrile (the middle layer) was recovered. The pentane solution was dried with anhydrous magnesium sulfate and the product was isolated by distillation: 12.58 g (81%), bp 75-77° C/45 mm Hg. 1H NMR CDCl3 δ ppm, 0.98 (d, J=6.6 Hz, 12H, CH3), 1.70 (s, 3H, CH3), 2.97 (m, 4H, CH2, CH), 4.78 (s, 1H,=CH2), 4.93 (m, 1H,=CH2) .
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