[H-].[Al+3].[Li+].[H-].[H-].[H-].[S:7]1[CH:11]=[CH:10][C:9]2[C:12]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24](OCC)=[O:25])[CH2:18][CH2:17]3)=[CH:13][CH:14]=[CH:15][C:8]1=2.O.[OH-].[Na+]>O1CCCC1>[S:7]1[CH:11]=[CH:10][C:9]2[C:12]([N:16]3[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][CH2:24][OH:25])[CH2:20][CH2:21]3)=[CH:13][CH:14]=[CH:15][C:8]1=2Lithium aluminum hydride (1.18 g, 24.8 mmol) was added to a solution of 5.26 g (16.5 mmol) of ethyl 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propionate in tetrahydrofuran (55 ml) with cooling in an ice-bath, followed by stirring at room temperature for 4 hours. Water (1.2 ml), 15% sodium hydroxide aqueous solution (1.2 ml), and water (3.6 ml) were added to the reaction mixture in this order with stirring at room temperature. Insoluble matters were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:2→ethyl acetate), then concentrated and dried under reduced pressure to obtain 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propane-1-ol (0.23 g) as white powder.
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