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19.18: Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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Organic Chemistry

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Preparation of Amines: Reductive Amination of Aldehydes and Ketones
 
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19.18: Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.

Figure1

Reductive amination using sodium cyanoborohydride as the reducing agent is called the Borch reaction. Sodium cyanoborohydride is a mild reductant that works under mildly acidic conditions.

Reductive amination has several applications, such as synthesizing the central nervous stimulant amphetamine and biosynthesis of the amino acid proline.

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Preparation Of Amines Reductive Amination Aldehydes Ketones Carbonyl Compounds Primary Amines Imines Secondary Amines Selective Reducing Agents Sodium Cyanoborohydride Sodium Triacetoxyborohydride Degrees Of Substitution Borch Reaction Mildly Acidic Conditions Central Nervous Stimulant Amphetamine Biosynthesis Amino Acid Proline

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