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Updated: Jun 10, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

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アミンの選択的モノアルキル化によるモルフォリンの緑色合成

Kacey G Ortiz1, Andrew T Brusoe1, Jason An1

  • 1Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, Connecticut 06877-0368, United States.

Journal of the American Chemical Society
|October 17, 2024
PubMed
まとめ

新しい効率的な方法は,エチレン硫酸塩を使用して1,2-アミノアルコールからモルフォリンを合成します. このシンプルで高生産性のプロトコルは 医薬品や農業に不可欠な化合物を 作るための従来の方法よりも 環境と安全性の利点をもたらします

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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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