Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF8 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This is more of a problem during the reductive methylation of amino acids because amino acids that are readily soluble in water are difficult to separate from aqueous solutions

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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

Experimental program
Comparison scheme
Effect test

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.

[0102]

[0103]

[0104]

[0105]

[0106]

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com