[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:14][CH2:13]1)#[N:8].O.[OH-].[K+]>CCOCC>[NH2:8][CH2:7][CH2:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][N:15]([C:18]2[N:19]=[CH:20][CH:21]=[CH:22][N:23]=2)[CH2:16][CH2:17]1
To a cold mixture of lithium aluminum hydride (2.0 g; 5.26 mmol) and anhydrous ether (240 ml) kept at a temperature of -54° C., there was dropwise added a solution of 1-(3-cyanopropyl)-4-(2-pyrimidinyl)piperazine (8 g; 3.46 mmol) in anhydrous ether (80 ml), and the resultant mixture was kept at the same temperature as above for 1.5 hours, followed by dropwise addition of water (2 ml), a 15% aqueous potassium hydroxide solution (2 ml) and water (6 ml) in order. The reaction mixture was stirred at room temperature for 2 hours, subjected to filtration with celite and washed with chloroform. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography to give 1-(4-aminobutyl)-4-(2-pyrimidinyl)-piperazine. IR νmaxFilm (cm--1): 3100-3600, 1580, 1540.
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