[O:1]=[C:2]1[C:7](=O)[CH:6]([C:9]#[N:10])[CH2:5][CH2:4][N:3]1[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.Cl.[NH2:19][NH2:20].C(O)(=O)C>C(O)C>[NH2:10][C:9]1[C:6]2[CH2:5][CH2:4][N:3]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[C:2](=[O:1])[C:7]=2[NH:20][N:19]=12,3-Dioxo-1-p-tolylpiperidine-4-carbonitrile (3.56 g, 15.597 mmol) was added to anhydrous ethanol (52.0 mL) and dissolved by heating to 60° C. After adding hydrazine hydrochloride (1.06 mL, 21.836 mmol) and glacial acetic acid (1.34 mL, 23.396 mmol) room temperature, reaction was carried out for 2 days. After removing ethanol by distillation, the produced solid was filtered and then acetic acid was completely removed by washing with NaHCO3 twice or more times. A target compound (3.25 g, 13.414 mmol, 86.0%) was yielded as white solid.
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