Ethanol → N-(Hex-5-en-1-yl)hex-5-en-1-amine

Next, ethanol (8.6 ml) and potassium hydroxide (0.85 g, 13 mmol) were added to 3-(di-5-hexenyl)aminopropionitrile (2.0 g, 8.6 mmol), and the obtained mixture was refluxed for 7.5 hours. The reaction mixture was allowed to stand, then water (150 ml) and chloroform (150 ml) were added to the reaction mixture. After separation, the organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the resulting residue was purified by basic silica gel column chromatography to give the target compound (0.32 g, 21%) as a pale yellow oily matter.