[N:1]1([CH2:7][C:8](=[CH2:11])[C:9]#[N:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:12]1([NH:18][NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[O-]CC.[Na+].Cl>C(O)C>[N:1]1([CH2:7][CH:8]2[CH2:11][N:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:19][C:9]2=[NH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1α-Piperidinomethylacrylonitrile (17g) and phenylhydrazine (10.8g) were added to a solution of sodium ethoxide (2.3g sodium) in ethanol (200 ml). The resulting solution was boiled under reflux for 2 hours and a solid precipitate formed during the reaction. Dilute hydrochloric acid (50 ml of 2N) was added to the reaction mixture and the solution was evaporated to dryness. The solid residue was extracted with dry ethanol and the product crystallised from the ethanol as colourless plates (melting point 186-7° C).
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