Method for preparing N,N-dimethyl-(R)-1-[(S)-2-(diphenylphosphine)ferrocenyl]ethylamine by microreactor

A technology of ferrocene and diphenylphosphine, which is applied in the field of N preparation, can solve the problems of complex reaction operation process and by-product generation, and achieve the effects of improving reaction efficiency, improving yield and reducing cost.

Active Publication Date: 2018-08-28
XIAN MODERN CHEM RES INST
View PDF2 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This method is operated in a traditional glass reactor. When n-butyllithium is added dropwise, nitrogen protection is required, and the system will heat up significantly. It is necessary to control the dropping rate ...

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
  • Method for preparing N,N-dimethyl-(R)-1-[(S)-2-(diphenylphosphine)ferrocenyl]ethylamine by microreactor
  • Method for preparing N,N-dimethyl-(R)-1-[(S)-2-(diphenylphosphine)ferrocenyl]ethylamine by microreactor
  • Method for preparing N,N-dimethyl-(R)-1-[(S)-2-(diphenylphosphine)ferrocenyl]ethylamine by microreactor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Raw material storage tanks 1 and 4 are respectively the methyl tert-butyl ether solution of N,N-dimethyl-(R)-1-[(S)-ferrocenyl]ethylamine (mass fraction 15% ) and n-butyllithium in n-hexane (2.7M), the methyl tert-butyl group of N,N-dimethyl-(R)-1-[(S)-ferrocenyl]ethylamine is controlled by a metering pump The flow rate of the ether solution is 50mL / min, and the flow rate of n-butyllithium n-hexane solution is 12mL / min, which is injected into the constant temperature module of the microchannel reactor and treated at a constant temperature of 25°C; after the constant temperature treatment, it enters the first mixing module of the microchannel reactor for Reaction, reaction temperature 25°C, residence time 7.1s.

[0027] (2) The effluent of the first mixing module is reacted with diphenylphosphine chloride in the second mixing module, the flow rate of diphenylphosphine chloride is controlled by a metering pump to be 7mL / min, the reaction temperature is 35°C, and the ...

Embodiment 2

[0030] (1) Raw material storage tanks 1 and 4 are respectively the methyl tert-butyl ether solution of N,N-dimethyl-(R)-1-[(S)-ferrocenyl]ethylamine (mass fraction 15% ) and n-butyllithium in n-hexane (2.7M), the methyl tert-butyl group of N,N-dimethyl-(R)-1-[(S)-ferrocenyl]ethylamine is controlled by a metering pump The flow rate of ether solution is 50mL / min, and the flow rate of n-butyllithium n-hexane solution is 14mL / min, which is injected into the constant temperature module of the microchannel reactor for constant temperature treatment at 25°C; after constant temperature treatment, it enters the first mixing module of the microchannel reactor for Reaction, reaction temperature 25°C, residence time 10.7s.

[0031] (2) The effluent of the first mixing module is reacted with diphenylphosphine chloride in the second mixing module, the flow rate of diphenylphosphine chloride is controlled by a metering pump to be 7mL / min, the reaction temperature is 35°C, and the Time 9.8s....

Embodiment 3

[0034] (1) Raw material tanks 1 and 4 are respectively the methyl tert-butyl ether solution of N,N-dimethyl-(R)-1-[(S)-ferrocenyl]ethylamine (mass fraction 20% ) and n-butyllithium in n-hexane (1.8M), the methyl tert-butyl group of N,N-dimethyl-(R)-1-[(S)-ferrocenyl]ethylamine is controlled by a metering pump The flow rate of the ether solution is 75mL / min, and the flow rate of n-butyllithium n-hexane solution is 39mL / min, which is injected into the constant temperature module of the microchannel reactor and treated at a constant temperature of 25°C; after the constant temperature treatment, it enters the first mixing module of the microchannel reactor for Reaction, reaction temperature 25°C, residence time 3.6s.

[0035] (2) React the effluent of the first mixing module with diphenylphosphine chloride in the second mixing module, the flow rate of diphenylphosphine chloride is controlled by a metering pump to be 12mL / min, the reaction temperature is 35°C, and the Time 3.4s. ...

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 discloses a method for preparing N,N-dimethyl-(R)-1-[(S)-2-(diphenylphosphine)ferrocenyl]ethylamine by a continuous flow microchannel reactor. The method comprises the following steps that an organic solvent solution of N,N-dimethyl-(R)-1-[(S)-2-ferrocenyl]ethylamine and an n-hexane solution of n-butyllithium are respectively introduced into a microchannel reactor constant temperature module by a metering pump for constant temperature treatment; then, the solutions enter a first mixing module for reaction; after the reaction is completed, the mixed solution enters a second mixingmodule to react with chlorodiphenylphosphine; acidification, extraction, drying and distillation are performed to obtain a crude product of the product of N,N-dimethyl-(R)-1-[(S)-2-(diphenylphosphine)ferrocenyl]ethylamine; the crude product is subjected to alcohol recrystallization to obtain the product of N,N-dimethyl-(R)-1-[(S)-2-(diphenylphosphine)ferrocenyl]ethylamine. The method has the advantages that the operation is simple, convenient and safe; the yield is high.

Description

technical field [0001] The invention relates to the field of synthesis of chiral organic small molecule catalysts, in particular to the preparation of N,N-dimethyl-(R)-1-[(S)-2-(diphenylphosphine) in a continuous flow microchannel reactor Ferrocenyl]ethylamine method. Background technique [0002] Chiral phosphine ligands such as Xyliphos, Josiphos, and TriFer with a ferrocene skeleton are widely used in the field of asymmetric catalytic hydrogenation (J.Am.Chem.Soc.2004,126,9918.; Angew.Chem.Int. Ed.2007, 46, 4141), especially Xyliphos, a high-efficiency ligand, gave a conversion number of 2 million in the imine hydrogenation reaction, and the ee value of the hydrogenated product was 79%. It has been successfully applied to the chiral herbicide Jindu The industrial production of Er (Xie Jianhua; Zhou Qilin.A ctaChim.Sinica 2012,70,1427—1438); N,N-dimethyl-(R)-1-[(S)-2-(diphenylphosphine) di Ferrocenyl]ethylamine is an important intermediate in the synthesis of such chiral...

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): C07F17/02
CPCC07F17/02
Inventor 杨翠凤陈涛徐泽刚毛明珍张晓光宁斌科苏天铎李秉擘王月梅卫天琪张媛媛
Owner XIAN MODERN CHEM RES INST
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