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Related Concept Videos

Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.8K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
2.8K
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

3.7K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
3.7K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

3.2K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
3.2K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.9K
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...
3.9K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.2K
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.
3.2K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.3K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
6.3K

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Related Experiment Video

Updated: Sep 30, 2025

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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Trichloroacetic acid fueled practical amine purifications.

Aleena Thomas1, Baptiste Gasch1, Enzo Olivieri1

  • 1Aix-Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France.

Beilstein Journal of Organic Chemistry
|March 14, 2022
PubMed
Summary

This study introduces a novel amine purification method using trichloroacetic acid (TCA). This technique significantly reduces waste and operational steps, offering a more efficient way to isolate pure amines.

Keywords:
aminesdecarboxylationeco-compatibleout of equilibriumpurification

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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants
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Area of Science:

  • Organic Chemistry
  • Chemical Engineering
  • Green Chemistry

Background:

  • Traditional amine purification methods are often inefficient, generating substantial waste.
  • There is a need for more sustainable and streamlined chemical purification processes.

Purpose of the Study:

  • To develop a novel, waste-reducing purification technique for amines.
  • To simplify amine isolation using readily available reagents.

Main Methods:

  • Utilizing trichloroacetic acid (TCA) to precipitate amines via protonated salt formation.
  • Employing decarboxylation of TCA to liberate pure amines and volatile byproducts.

Main Results:

  • Successful isolation of a diverse range of substituted amines.
  • Demonstrated significant reduction in operational steps and waste generation compared to conventional methods.

Conclusions:

  • The developed TCA-based method offers an efficient and greener alternative for amine purification.
  • This approach is broadly applicable to various substituted amines, simplifying their isolation.