[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.O1CCCC1.[OH-].[Na+]>O>[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 a tetrahydrofuran (THF) solution (55 ml) under ice cooling, and the mixture was stirred at room temperature for 4 hours. To the reaction solution, water (1.2 ml), 15% aqueous sodium hydroxide solution (1.2 ml), and water (3.6 ml) were added in this order and the mixture was stirred at room temperature. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:2→ethyl acetate) and concentrated to dryness under reduced pressure to obtain 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propan-1-ol (0.23 g) as white powder.
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