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Synthesis 1991; 1991(9): 703-708
DOI: 10.1055/s-1991-26551
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Convenient Preparations of Imines and Symmetrical Secondary Amines Possessing Primary or Secondary Alkyl Groups

Alan R. Katritzky* , Xiaohong Zhao, Gregory J. Hitchings
  • *Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
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Publication Date:
29 April 2002 (online)

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Hindered alkyl aldehydes react with benzotriazole and ammonia in dry ethanol or methanol to yield the corresponding bis[1-(benzotriazol-1-yl)alkyl]amines 2. The reaction of aryl aldehydes, however, yields 1-(benzotriazol-1-yl)-N-alkylidenealkylamines 3. The reactions of adducts 2 and 3 with lithium aluminum hydride furnishes dialkyl- and dibenzylamine derivatives 4. Although the reactions of 2 and 3 with organometallic reagents are not as general, in several cases the reactions of amines 2 with Grignard reagents yield 1-alkyl or aryl substituted N-alkylidenealkylamines 5. Similar reactions of amines 2 with phenyl lithium afford 1,1′-diphenyldialkylamines 7.