[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18])[CH:8]=1.O.[OH-].[Na+]>CCOCC.C1COCC1>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH:8]=1
To 2.9 g (0.073 mol) of lithium aluminum hydride stirred at 25° in 100 ml of anhydrous ether at 25° was added dropwise 4.7 g (0.029 mol) of 4-(3-pyridinyloxy)butyronitrile in 30 ml of ether and 20 ml anhydrous THF over 15 minutes. The reaction mixture was then stirred at reflux for 3.5 hours, cooled in an ice bath during the addition of 3 ml of H2O, followed by 3 ml of 15% NaOH solution and finally 9 ml of H2O. The granular solid was filtered, washed with CHCl3 and the filtrate was concentrated in vacuo. The residue was dissolved in CHCl3, washed with H2O, dried (MgSO4) and concentrated in vacuo to an oil. Distillation gave 2.6 g., b.p. 103°-107°/0.5 mm (53% yield) of the desired amine which was analyzed as the dihydrochloride obtained from 2-propanol-ether, m.p. 127°-131° .
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