[CH2:1]([N:13]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[CH2:1]([N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]56.2g (0.2 mol) of 1-dodecylazacycloheptan-2-one in 100ml diethyl ether was added dropwise to a suspension of 7.6g (0.2 mol) lithium aluminum hydride in 100ml diethyl ether under argon at room temperature. After 5 hours of stirring, 20ml saturated sodium sulfate was added dropwise. The mixture was filtered and the filtrate was dried with magnesium sulfate, filtered and concentrated. The resulting oil was distilled (130°/0.03 mm) to yield 50.03g (93.5%) of 1-n-dodecylazacycloheptane.
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