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A Simple Secondary Amine Synthesis: Reductive Amination Using Sodium Triacetoxyborohydride

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Merle W. Carlson , James T. Ciszewski , Micah M. Bhatti , Wesley F. Swanson and Anne M. Wilson

Department of Chemistry, Butler University, Indianapolis, IN 46208

J. Chem. Educ., 2000, 77 (2), p 270

DOI: 10.1021/ed077p270

Publication Date (Web): February 1, 2000

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Synthesis

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

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  The synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide is a fast, simple three-step sequence that serves as a useful example of the reductive amination reaction for the organic chemistry laboratory. The first step is a spectacular solvent-free ...
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