[CH3:1][NH:2][CH3:3].[CH3:4][O:5][C:6]1[CH:20]=[CH:19][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([CH:17]=O)[CH2:13][CH2:12]2)=[CH:8][CH:7]=1.[C-:21]#[N:22].[K+].Cl>O.CO>[CH3:1][N:2]([CH3:3])[CH:17]([CH:14]1[CH2:15][CH2:16][N:11]([CH2:10][C:9]2[CH:19]=[CH:20][C:6]([O:5][CH3:4])=[CH:7][CH:8]=2)[CH2:12][CH2:13]1)[C:21]#[N:22]40% strength aqueous dimethylamine solution (2.66 ml, 21 mmol), 1-(4-methoxybenzyl)piperidine-4-carbaldehyde (750 mg, 3.2 mmol) and potassium cyanide (688 mg, 10.6 mmol) were added to a mixture of 4 N hydrochloric acid (1.2 ml) and methanol (5 ml), while cooling with ice. The reaction mixture was stirred at room temperature for 5 d, water (50 ml) was then added and the mixture was extracted with ethyl acetate (3×50 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac.
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