Preparation method of N-phenylmethyl benzylamine

A technology of benzyl benzylamine and benzoic acid, which is applied in the field of catalysis, can solve the problems of high toxicity of C-N bond reagents, difficulty in reaching the industrial level, and aggravated environmental pollution, and achieve low production cost, no three wastes, and high atom economy Effect

Pending Publication Date: 2021-04-30
SHANGHAI INST OF TECH
View PDF2 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The traditional method C-N bond reagent is highly toxic, and some reactions will also produce stoichiometric metal salt waste or waste acid that aggravates environmental pollution and other problems
In the past two decades, organometallic catalysts hav

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
  • Preparation method of N-phenylmethyl benzylamine
  • Preparation method of N-phenylmethyl benzylamine
  • Preparation method of N-phenylmethyl benzylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Put 0.1072g of benzyl ammonium, 0.1222g of benzoic acid, 0.1-2.0mol% of Anderson type polyoxometalate with Ni as the central metal, 2.0-6.0equiv of phenylsilane, and 2.0-6.0mL of solvent toluene into the drying In the reaction tube, the reaction tube is covered with a balloon, and the reaction temperature is controlled at 80-120°C. After 18 hours of heat preservation, the reaction is stopped, cooled to room temperature, and the sample is prepared for GC-MS detection. The result of GC-MS is the conversion rate of the reaction substrate 96%. After separation and purification, NMR test was carried out, and it was proved to be N-benzylbenzylamine from the obtained hydrogen spectrum and carbon spectrum data.

Embodiment 2

[0028] Put 0.1072g of benzyl ammonium, 0.1222g of benzoic acid, 0.1-2.0mol% of Al as the center metal Anderson type polyoxometalate, 2.0-6.0equiv of phenylsilane, 2.0-6.0mL of solvent toluene into the drying In the reaction tube, the reaction tube is covered with a balloon, and the reaction temperature is controlled at 80-120°C. After 18 hours of heat preservation, the reaction is stopped, cooled to room temperature, and the sample is prepared for GC-MS detection. The result of GC-MS is the conversion rate of the reaction substrate 83%. After separation and purification, NMR test was carried out, and it was proved to be N-benzylbenzylamine from the obtained hydrogen spectrum and carbon spectrum data.

Embodiment 3

[0030] Put 0.1072g of benzyl ammonium, 0.1222g of benzoic acid, 0.1-2.0mol% of Cr as the center metal Anderson type polyoxometalate, 2.0-6.0equiv of phenylsilane, and 2.0-6.0mL of solvent toluene into the drying In the reaction tube, the reaction tube is covered with a balloon, and the reaction temperature is controlled at 80-120°C. After 18 hours of heat preservation, the reaction is stopped, cooled to room temperature, and the sample is prepared for GC-MS detection. The result of GC-MS is the conversion rate of the reaction substrate 91%. After separation and purification, NMR test was carried out, and it was proved to be N-benzylbenzylamine from the obtained hydrogen spectrum and carbon spectrum data.

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 invention relates to a preparation method of N-phenylmethyl benzylamine, which is characterized by comprising the following steps of by using polyoxometallate as a catalyst, putting into a reaction container, sequentially adding an organic solvent, benzylamine and benzoic acid into the container, finally adding an additive, heating, stirring, reacting, and separating to obtain the N-phenylmethyl benzylamine. After the reaction is finished, the catalyst can be recycled, the system after the reaction is finished is directly filtered, the polyoxometallate can be directly filtered out and recycled after being treated, and the recycled polyacid is used for preparing the N-phenylmethyl benzylamine. Compared with the prior art, the method has the advantages that benzylammonium and benzoic acid can react to prepare N-phenylmethyl benzylamine, high activity and high selectivity are achieved, reaction conditions are mild, environment friendliness is achieved, the catalyst can be recycled, and great industrial production potential is achieved.

Description

technical field [0001] The invention relates to the technical field of catalysis, in particular to a preparation method of N-benzylbenzylamine. Background technique [0002] Amines and their derivatives widely exist in basic and commercially important molecules, and are important structural units of many biologically active molecules, and widely exist in chemical drugs, natural products and functional materials. The focus of attention from industry and academia. So far, there are many methods to construct carbon-nitrogen bonds, such as N-alkylation, Ullmann coupling, Buchwald–Hartwig coupling, Goldberg coupling reaction and hydroamination. [0003] The C-N bond is one of the most important structural motifs in nature, which exists in natural products, proteins and therapeutic drugs, and is of great significance in organic chemistry and biochemistry. In addition, according to statistics, about 25% of the drugs on the global market contain at least one C-N group, including s...

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): C07C211/27C07C209/46B01J31/18B01J27/188
CPCC07C209/46B01J27/188C07C211/27Y02P20/584
Inventor 陶朝富常亚林谢雅王爱萍余焓
Owner SHANGHAI INST OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap