C([SiH](CC)CC)C.[CH2:8]([CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]#[N:18])[CH2:12][CH2:11]1)[CH3:9].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[ClH:27]>CCOCC.O>[ClH:27].[CH2:8]([CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][NH2:18])[CH2:12][CH2:11]1)[CH3:9]The title compound was prepared according to general procedure H described in Scheme 3. The crude triethylsilane solution of 2-(4-ethylpiperidin-1-yl)acetonitrile was added carefully to a slurry of LiAlH4 (8.3 equiv., 1.2 g, 31 mmol) in ether (5 mL) and stirred at RT under Ar for 14 h. The crude reaction mixture containing a white precipitate was cooled to 0° C. and treated dropwise with 10% aqueous NaOH (1 mL) and stirred for 30 min. The cooled mixture was treated with H2O (2.1 mL) to provide a thick precipitate. The mixture was then treated with ether (10 mL), stirred and filtered. The filter cake was washed with ether (5×10 mL). The combined ether layer was concentrated under reduced pressure to provide a concentrated solution in ether/H2O that was acidified to pH 2 with 1 N HCl. The mixture was concentrated under reduced pressure to provide 2-(4-ethylpiperidin-1-yl)ethanamine hydrochloride as a brown oil (200 mg, 28% yield).
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