Reductive alkylation of amines with orthocarboxylic acid esters

A carboxylate, alkylation technology, applied in reductive alkylation preparation, organic chemistry, cyanide reaction preparation, etc., can solve problems such as difficult separation of amino acids

Active Publication Date: 2018-09-28
EVONIK OPERATIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This is more of a problem during the reductive methylation of amino acids because amino

Method used

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  • Reductive alkylation of amines with orthocarboxylic acid esters
  • Reductive alkylation of amines with orthocarboxylic acid esters
  • Reductive alkylation of amines with orthocarboxylic acid esters

Examples

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Embodiment Construction

[0099] General procedure for the reductive alkylation of amines with orthocarboxylates

[0100] Fill the autoclave with catalyst (1 mol%, based on the molar amount of amine), flush with argon and add amine (0.1 mol) and orthocarboxylate (0.11-0.3 mol) in 10 ml of methanol (or ethanol) solution and 0.5ml of 0.2M anhydrous p-toluenesulfonic acid in methanol (or ethanol). The mixture was heated to 120° C. and injected with hydrogen to 40 bar, then the mixture was stirred at constant pressure until no more hydrogen uptake could be detected (0.2-6 hours). After filtering off the catalyst, the filtrate was distilled.

[0101] Yields can be found in Table 1.

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Abstract

The present invention relates to a process for the N-alkylation of amines by reacting an amine with an orthocarboxylic acid ester and with hydrogen in the presence of a hydrogenation catalyst.

Description

technical field [0001] The present invention relates to a process for the preparation of amines by reductive alkylation of amines or ammonia by means of orthocarboxylates in the presence of hydrogen and a hydrogenation catalyst. Background technique [0002] Amines play a dominant role in many complex natural substances, such as alkaloids, vitamins or amino acids, and their chemical, pharmaceutical and industrial importance is undeniable. As intermediates, amines are used inter alia in the synthesis of pharmaceuticals, agrochemicals, food additives, dyes or cosmetics. For the field of active ingredients, amino acids play an excellent role in this. [0003] Amines can especially be prepared by reduction of the corresponding carboxamides, for example by catalytic hydrogenation of carboxamides (M. Steinand B. Breit, Angew. Chem. Int. Ed. 2013, 52, 2231-2234; WO 2015 / 067450 A1) Or by catalytic hydrogenation of amide acetals, enone N,O-acetals or ester imides (WO 2015 / 067448 A1...

Claims

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Application Information

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IPC IPC(8): C07C209/26C07C227/18C07D207/16C07D295/023C07D211/60C07C211/48C07C211/27C07C229/12C07C229/36C07C229/24
CPCC07C209/26C07C227/18C07D295/023C07D295/03C07C211/48C07C211/27C07C229/12C07C229/36C07C229/24C07D207/06C07D211/16C07D265/30
Inventor R·卡德罗夫
Owner EVONIK OPERATIONS GMBH
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