HRID2225961
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Chem. Ber. 1966, 3387 to 3389 discloses the preparation of 1,5-diaminohexane from 5-oxocapronitrile. In this process, 1,5-diaminohexane is only obtained via the oxime intermediate by first reacting 5-oxocapronitrile with hydroxylamine hydrochloride in the presence of anhydrous sodium carbonate to give 5-oximinocapronitrile, which is subsequently reacted with lithium aluminum hydride to give the diamine; the overall yield is 42%. According to the authors, direct reductive amination of 5-oxocapronitrile gives the cyclization product, 2-methylpiperidine.