[O:1]1[C:9]2[CH2:8][CH2:7][N:6]([C:10](=[O:20])[CH2:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:5][C:4]=2[CH:3]=[CH:2]1.[CH3:21][NH:22][CH3:23].[CH2:24]=O>C(O)(=O)C>[CH3:21][N:22]([CH2:24][C:2]1[O:1][C:9]2[CH2:8][CH2:7][N:6]([C:10](=[O:20])[CH2:11][CH2:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:5][C:4]=2[CH:3]=1)[CH3:23]To a solution of 0.160 g (0.594 mmol) of 1-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-4-phenylbutan-1-one in 20 ml of acetic acid, 0.080 ml (0.88 mmol) of 50% aqueous dimethylamine and 0.072 ml (0.88 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 30 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1) to yield the desired product.
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