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  Home > JCE Print > Journal of Chemical Education > Issues > 2000  > February  >
In the Laboratory
A Simple Secondary Amine Synthesis: Reductive Amination Using Sodium Triacetoxyborohydride
Merle W. Carlson, James T. Ciszewski, Micah M. Bhatti, Wesley F. Swanson, and Anne M. Wilson
Department of Chemistry, Butler University, Indianapolis, IN 46208
Cover
February 2000
Vol. 77 No. 2
p. 270
Abstract
We present a reductive amination experiment for a second-semester organic chemistry class. It utilizes an imine intermediate and sodium triacetoxyborohydride, a mild reducing agent. The progress of the reaction is followed by TLC as the starting materials (the aldehyde and primary amine), the imine intermediate, and the secondary amine product are visible under ultraviolet light. This experiment provides an introduction to the observation of intermediates, the synthesis of amines, and the concept of mild reducing agents.
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Experimental procedures, sample spectra, and additional information are provided.
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*  Citation
 Carlson, Merle W.; Ciszewski, James T.; Bhatti, Micah M.; Swanson, Wesley F.; Wilson, Anne M. J. Chem. Educ. 2000 77 270.
*  Keywords
 Organic Chemistry; Organic Synthesis; Chromatography; Laboratory Instruction
*  History
 Created:
Last Updated:		 January 5, 2000
August 31, 2005
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