Preparation of imidazole type ionic liquid derived by cinchona alkaloid

An ionic liquid, cinchona base technology, applied in physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, organic chemistry and other directions, can solve the problem of unreasonable utilization of resources, large amount of catalyst, and inability to recycle and other problems, to achieve the effects of easy separation, recovery and recycling, high raw material utilization, and easy operation.

Inactive Publication Date: 2016-02-17
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] At present, catalysts used for asymmetric reactions, such as noble metal complexes, natural enzymes, etc., have good catalytic activity, but the amount of catalyst used is large and cannot be recycled, which will easily lead to unreasonable utilization of resources and serious waste of raw materials

Method used

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  • Preparation of imidazole type ionic liquid derived by cinchona alkaloid
  • Preparation of imidazole type ionic liquid derived by cinchona alkaloid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] The first step: Weigh 8.68g of Quinine and 2.98g of triethylamine and dissolve them in 40ml of tetrahydrofuran. Dissolve 5.02g of p-chloromethylbenzoyl chloride in 5ml of tetrahydrofuran. The tetrahydrofuran solution was slowly dropped dropwise into the tetrahydrofuran solution of quinine triethylamine. After the dropwise addition, the reaction was carried out at normal temperature and normal pressure for 12 hours. After the reaction was monitored by TLC, the solvent was spin-dried. Mixed and extracted, the aqueous phase was extracted twice with 40 ml of dichloromethane, the organic phases were combined and extracted once with 30 ml of saturated NaCl solution, and an appropriate amount of anhydrous Na was added. 2 SO 4 Drying, then filtering, concentrating the filtrate and silica gel column chromatography (EA:PE=1:5) to obtain the 9-hydroxyl-modified compound of cinchonadine as benzyl chloroalkane (QN-Cl) (3-(4-( ((R)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinu...

Embodiment 2

[0017] The first step: Weigh 4.15g of Quinidine (Quinidine) and 1.53g of triethylamine and dissolve them in 20ml of acetonitrile, dissolve 2.46g of p-chloromethylbenzoyl chloride in 3ml of tetrahydrofuran, and at 0 ℃ temperature, The tetrahydrofuran solution of the acid chloride was slowly dropped dropwise into the acetonitrile solution of quinidine triethylamine. After the dropwise addition, the reaction was carried out at normal temperature and normal pressure for 16 hours. After the reaction was monitored by TLC, the solvent was spin-dried. Mixed and extracted with equal volume of water, the aqueous phase was extracted twice with 40 ml of dichloromethane, the organic phases were combined and extracted once with 30 ml of saturated NaCl solution, and an appropriate amount of anhydrous Na was added. 2 SO 4 Dry, then filter, concentrate the filtrate and silica gel column chromatography (EA:PE=1:3) to obtain the compound as benzyl chloroalkane (QD-Cl) (3-(4-(((S)-(6-methoxyquino...

Embodiment 3

[0021] The first step: Weigh 8.59g of Cinchonine and 3.24g of triethylamine and dissolve them in 50ml of dimethylformamide (DMF). Under the temperature of ℃, the tetrahydrofuran solution of the acid chloride was slowly dropped dropwise into the DMF solution of quinidine triethylamine, after the dropwise addition, the reaction was carried out at normal temperature and normal pressure for 16 hours, and the solvent was spin-dried after the reaction was monitored by TLC. Ethyl acetate, diluted with 200ml of distilled water, the precipitated white solid was collected by filtration, the filtrate was re-separated, the aqueous phase was extracted twice with 40ml of ethyl acetate, the combined organic phases were extracted once with 20ml of saturated NaCl solution, and an appropriate amount of anhydrous Na 2 SO 4 Dry, then filter, concentrate the filtrate and silica gel column chromatography (EA:PE=1:5) to obtain the compound as benzyl chloride (CN-Cl)(1-methyl-3-(4-(((S)- quinolin-4-...

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Abstract

The invention discloses the preparation of imidazole type ionic liquid derived by cinchona alkaloid. The preparation is characterized by adopting quinine or cinchonine to modify 9-hydroxyl of the cinchona alkaloid; carrying out a replacement reaction on chloride salt of obtained imidazole type ionic liquid and inorganic metal salt; preparing imidazole type ionic liquid catalysts of different anions. Compared with the prior art, the preparation disclosed by the invention has the advantages that the catalytic activity is high, the catalysts are easily separated and recycled and can be reused again, the preparation is simple, post-processing is easy, the stability of the catalysts is greatly increased, the application range of the catalysts in a micromolecular organic asymmetric reaction is expanded, reaction conditions are optimized, reaction requirements are reduced, the catalytic activity and the enantioselectivity of a chiral imidazole type ionic liquid catalyst in an asymmetric reaction are further increased, and great significance is obtained for researching medicinal chemistry and medical intermediate compounds.

Description

technical field [0001] The invention relates to the technical field of organic catalysts, in particular to the preparation of an imidazole type ionic liquid derived from cinchona base used in asymmetric reactions. Background technique [0002] At present, catalysts for asymmetric reactions, such as noble metal complexes, natural enzymes, etc., have good catalytic activity, but the amount of catalyst is large and cannot be recycled, which easily leads to unreasonable utilization of resources and serious waste of raw materials. In recent years, the application of small molecular organocatalysts in asymmetric reactions has received extensive attention, especially cinchonaine and its derivatives have shown good catalytic activity in asymmetric Michael reaction, asymmetric Friedel-Crafts reaction and other reactions. and enantioselectivity are also getting more and more attention. Although such small molecule catalysts have the advantages of simple preparation process, cheap raw...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D453/04B01J31/02
CPCB01J31/0284B01J31/0285C07D453/04
Inventor 吴海虹刘廷英吴鹏
Owner EAST CHINA NORMAL UNIV
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