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Synthesis 1991; 1991(6): 447-450
DOI: 10.1055/s-1991-26489
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Reductive One Batch Synthesis of N-Arylpiperidines From Primary Amines and Glutaraldehyde

Giancarlo Verardo* , Angelo G. Giumanini, Grazia Favret, Paolo Strazzolini
  • *Department of Chemistry, University of Udine, I-33100 Udine, Italy
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Publication Date:
29 April 2002 (online)

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The construction of the piperidine ring about an aromatic nitrogen atom, by a 5C + N reductive condensation reaction, using glutaraldehyde (pentanedial) and sodium borohydride in acidic water/methanol medium is described. The reaction is fast, affords good to excellent yields and appears insensitive to electronic effects and severe steric hindrance; it is found to be compatible with a large variety of aryl substituents, including nitro and oxo groups.