CCOC(C)=O.[O:7]=[C:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18][N:19]3[CH2:24][CH2:23][CH:22]([NH:25]C(=O)OC(C)(C)C)[CH2:21][CH2:20]3)=[CH:13][CH:14]=2)[NH:9]1.Cl.CCOC(C)=O.C(Cl)(Cl)Cl>O>[NH2:25][CH:22]1[CH2:23][CH2:24][N:19]([CH2:18][C:12]2[CH:11]=[C:10]3[C:15]([CH2:16][CH2:17][C:8](=[O:7])[NH:9]3)=[CH:14][CH:13]=2)[CH2:20][CH2:21]1To an EtOAc (130 mL) solution of the compound (37.8 g) obtained in Step 1-5, 4 M HCl/EtOAc solution (263 mL) was added under ice cooling and the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure. The residue was suspended in EtOAc (200 mL) and filtrated to obtain a solid. To the solid, CHCl3 (200 mL) and H2O (200 mL) were added and the mixture was stirred for 15 minutes. After a water layer and an organic layer were separated, the water layer was washed with CHCl3 twice. To the water layer, a 2 M aqueous NaOH solution was added to adjust to pH 10 and thereafter the solution was extracted 30 times with CHCl3. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (Chromatorex NH, mobile phase: MeOH/CHCl3=1/4; v/v) to obtain 7-[(4-aminopiperidin-1-yl)methyl]-3,4-dihydroquinolin-2(1H)-one (17.9 g, a colorless solid).
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