Method for catalysis of N-methylation of amines by using iridium complex with methanol as carbon source

A technology of iridium complex and methylation, which is applied in the field of energy and homogeneous catalysis, can solve the problems of low reaction selectivity, difficult separation and purification, etc., and achieve the effect of simple preparation method, high economic applicability and low cost

Inactive Publication Date: 2019-10-25
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, the use of dangerous and highly toxic methylation reagents; the use of strong alkaline reaction media poses more risks to downstream processing equipmen...

Method used

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  • Method for catalysis of N-methylation of amines by using iridium complex with methanol as carbon source
  • Method for catalysis of N-methylation of amines by using iridium complex with methanol as carbon source
  • Method for catalysis of N-methylation of amines by using iridium complex with methanol as carbon source

Examples

Experimental program
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Embodiment 1

[0037] Example 1: Preparation of Cat.A and its method for catalyzing the N-methylation of amines.

[0038] (1) Under nitrogen atmosphere, N-phenylpyridinamide ligand (0.0159g, 0.08mmol) and [Cp*IrCl 2 ] 2 (0.0319g, 0.04mmol) was added to a 25mL single-necked bottle, 14mL of anhydrous methanol was added, and the temperature was raised to 65°C, and the reaction was stirred for 20h. After the reaction was completed, cooled to room temperature, the solvent was removed by rotary evaporation, and vacuum-dried to obtain 0.0455g of metal Iridium complex Cat.A.

[0039] (2) Under a nitrogen environment, weigh 5 μmol of the catalyst prepared in (1) and place it in a sample bottle, then add 0.5 mL of anhydrous methanol to prepare a catalyst methanol solution with a concentration of 10 μmol / mL, and store it under nitrogen protection for future use .

[0040] (3) Under nitrogen atmosphere, add 0.5mmol aniline, 0.15mmol (0.0488g) cesium carbonate, 0.5mL Cat.A methanol solution with a con...

Embodiment 2

[0041] Example 2: Preparation of Cat.B and its method for catalyzing the N-methylation of amines.

[0042] (1) Under nitrogen atmosphere, 6-hydroxyl-N-phenylpyridinamide ligand (0.0172g, 0.08mmol) and [Cp*IrCl 2 ] 2 (0.0319g, 0.04mmol) was added to a 25mL single-necked bottle, 14mL of anhydrous methanol was added, and the temperature was raised to 65°C, and the reaction was stirred for 24h. After the reaction was completed, cooled to room temperature, the solvent was removed by rotary evaporation, and vacuum-dried to obtain 0.0466g of metal Iridium complexes Cat.B.

[0043] (2) Prepare a catalyst methanol solution of 10 μmol / mL, the same as step (2) of Example 1.

[0044] (3) Under nitrogen atmosphere, add 0.5mmol aniline, 0.15mmol (0.0488g) cesium carbonate, 0.5mL Cat.B methanol solution with a concentration of 10μmol / mL, 0.5mL anhydrous methanol to the reaction tube, and then seal reaction tube. The gas in the reaction tube was replaced with nitrogen three times, and the...

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Abstract

The invention provides a method for catalysis of N-methylation of amines by using an iridium complex with methanol as a carbon source, and belongs to the technical field of energy and homogeneous catalysis. The methanol is used as the carbon source, and under the catalysis of the iridium complex, the reaction of N-methylation of various amine substrates is achieved. The method has the advantages that the methanol is used as the carbon source, toxicity is low, the cost is low, obtaining is easy, and economic applicability is higher; an only by-product is water, and requirements of green chemistry in nowadays society are met; the used preparation method of an iridium complex catalyst is easy, the cost is low, and stability is good; N-methylation of various primary amines and secondary aminescan be high-selectively achieved, and the product yield is excellent. The invention provides a green synthetic method for N-methylation reaction of the amines.

Description

technical field [0001] The invention belongs to the technical field of energy and homogeneous catalysis, and relates to homogeneously catalyzed N-methylation reactions of amines, in particular to a method for catalyzing the N-methylation of amines with methanol as a carbon source and using iridium complexes. Background technique [0002] The N-methylation reaction of amines is an important reaction to form C-N bonds, and N-methylamines exist in many important drug molecules and biologically active natural products. The direct N-methylation of amines is also one of the most important transformations in the synthesis of fine chemicals, drugs and natural products. There are a variety of N-methylated drug intermediates in different reaction stages during drug synthesis appear to varying degrees. Therefore, N-methylation reaction has received more and more attention. [0003] Methyl iodide, dimethyl sulfate or diazomethane are traditionally used as N-methylating reagents. Alth...

Claims

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Application Information

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IPC IPC(8): C07C209/18C07C211/48B01J31/22
CPCC07C209/18B01J31/2295B01J2531/827C07C211/48
Inventor 王万辉武锦渊刘平包明
Owner DALIAN UNIV OF TECH
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