Supercharge Your Innovation With Domain-Expert AI Agents!

A method for reducing tertiary amides to amines

A technology for tertiary amides and tertiary amine compounds, applied in the direction of organic reduction, organic chemical methods, chemical instruments and methods, etc., can solve problems such as harsh conditions, complicated operations, and difficult product control, and achieve environmentally friendly reactions, safe and simple operations, and Wide range of effects

Active Publication Date: 2021-02-09
CHINA AGRI UNIV
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a reduction method for tertiary amides, which solves the problems of complex operations, harsh conditions, and difficult control of the generated products in the reduction method of amides in the prior art, so that tertiary amides can be reduced to tertiary amines, This method does not use noble metal catalysts, toxic and harmful silanes, and flammable and explosive metal hydrides, and does not produce toxic by-products, making the reaction more environmentally friendly

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
  • A method for reducing tertiary amides to amines
  • A method for reducing tertiary amides to amines
  • A method for reducing tertiary amides to amines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051]

[0052] In a 10mL single-necked bottle, add 0.50mmol compound 1a, 2.5mL toluene, saturated aqueous sodium bicarbonate (H 2 (0:10mmol), 2.0mmol sodium dispersion reagent (34.1wt%, toluene suspension, particle size<100μm), stirred at 0°C for 30min, raised to room temperature, and quenched the reaction with saturated aqueous sodium bicarbonate solution. Diethyl ether and saturated brine were added for extraction, the organic phase was dried, concentrated, and separated by column chromatography to obtain 14 mg of the target compound 3a with a yield of 15%.

[0053] 1 H NMR (300MHz, CDCl 3 )δ7.31-7.22(m,2H),7.21-7.13(m,3H),2.65(t,J=7.8Hz,2H),2.53-2.41(m,6H),1.84(m,2H),1.80 -1.71(m,4H); 13 C NMR (75MHz, CDCl 3 )δ142.3, 128.4, 128.3, 125.7, 56.1, 54.2, 34.0, 30.7, 23.5.

Embodiment 2

[0055]

[0056] In a 10mL single-necked bottle, add 0.50mmol compound 1a, 2.5mL toluene, saturated aqueous sodium bicarbonate solution (D 2 O: 10mmol, 2.0mmol sodium dispersion reagent (34.1wt%, toluene suspension, particle size <100μm), stirred at 0°C for 30min, raised to room temperature, quenched with saturated aqueous sodium bicarbonate solution. Diethyl ether and saturated brine were added for extraction, the organic phase was dried, concentrated, and separated by column chromatography to obtain 28.7 mg of the target compound 5a with a yield of 30%.

[0057] 1 H NMR (300MHz, CDCl 3 )δ7.32-7.22(m,2H),7.22-7.13(m,3H),2.65(t,J=7.6Hz,2H),2.48(m,4H),1.84(t,J=7.6Hz,2H ),1.77(m,4H); 13 C NMR (75MHz, CDCl 3 )δ142.3, 128.4, 128.3, 125.7, 55.2(m), 54.1, 33.9, 30.4, 23.5.

Embodiment 3

[0059]

[0060] In a 10mL single-necked bottle, under nitrogen protection, add 0.50mmol compound 1b, 2.5mL tetrahydrofuran, 350g / L saturated aqueous sodium chloride (H 2 (0:10mmol), 10mmol sodium dispersion reagent (34.1wt%, mineral oil suspension, particle size<100μm), stirred at 0°C for 30min, raised to room temperature, and quenched with saturated aqueous sodium bicarbonate solution. Diethyl ether and saturated brine were added for extraction, the organic phase was dried, concentrated, and separated by column chromatography to obtain 71.2 mg of the target compound 3b with a yield of 69%.

[0061] 1 H NMR (300MHz, CDCl 3 )δ7.31-7.22(m,2H),7.21-7.13(m,3H),3.73-3.67(m,4H),2.63(t,J=7.7Hz,2H),2.46-2.38(m,4H) ,2.35(t,J=7.7Hz,2H),1.81(m,2H). 13 C NMR (75MHz, CDCl 3 )δ142.1, 128.4, 128.3, 125.8, 67.0, 58.4, 53.7, 33.6, 28.3.

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

PropertyMeasurementUnit
particle diameteraaaaaaaaaa
Login to View More

Abstract

The invention discloses a method for reducing a tertiary amide to an amine. The following reaction is completed by putting a tertiary amide, an alkali metal reagent and a proton donor reagent in an organic solvent: when the proton donor reagent is an aqueous solution of an inorganic salt, the reaction The product is a tertiary amine compound. The invention enables tertiary amides to be reduced to tertiary amine compounds, with high yield, wide application range, safe and simple operation; the raw materials used are cheap and easy to obtain, and do not involve noble metal catalysts, toxic and harmful silanes and flammable and explosive The metal hydride does not produce toxic by-products, and the reaction is more environmentally friendly, which can solve the problems in the prior art that the reduction method of amide compounds is complicated to operate, the conditions are harsh, and the generated products are difficult to control.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a reduction method for reducing tertiary amides to tertiary amines. Background technique [0002] Amines are one of the most common functional groups in pesticides, pharmaceuticals, and materials science. The reduction of amides in raw materials to amines has important research and application value. At the same time, in recent years, the development of deuterated compounds has attracted much attention, and their uses are very wide, and the demand is gradually increasing. In the pharmaceutical industry, the introduction of deuterium can improve the pharmacokinetic properties of the drug, increase the stability of the drug, and reduce the toxicity of the drug (J.Med.Chem.2011,54,2529-2591). The drug is officially on the market. In addition, deuterated compounds can be used as tools for studying chemical reaction mechanisms and internal standards in instrumental analysis. [00...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07B31/00C07B59/00C07C29/00C07C33/20C07C33/46C07C31/125C07C33/025C07C31/135C07C31/137C07C33/24C07D295/03C07D295/023C07C209/50C07C211/27C07C211/03C07C41/26C07C43/23C07D295/096C07D209/12C07C213/00C07C215/08C07C319/20C07C323/19
CPCC07B31/00C07B59/001C07B59/002C07B59/004C07B2200/05C07C29/00C07C41/26C07C209/50C07C213/00C07C319/20C07D209/12C07D295/023C07D295/03C07D295/096C07C33/20C07C33/46C07C31/125C07C33/025C07C31/135C07C31/137C07C33/24C07C211/27C07C211/03C07C43/23C07C215/08C07C323/19
Inventor 安杰李恒朝张斌阎昱好罗仕晖张运通
Owner CHINA AGRI UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com