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Preparation method of water-phase alkynyl amine compounds and product obtained by preparation method

A secondary amine compound and compound technology are applied in the field of preparation of aqueous alkyne amine compounds, which can solve the problems of inflammability and explosion, solvent pollution, climate change, etc., and achieve the effects of simple operation, mild conditions and wide substrate range.

Inactive Publication Date: 2019-12-03
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As we all know, in the field of organic synthesis, the organic solvents used by people have serious problems such as strong toxicity, refractory degradation, flammability and explosion, and climate change. Therefore, the inevitable solvent pollution problem needs to be solved, and a green and efficient alkyne amine is developed. The method of synthesis is crucial

Method used

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  • Preparation method of water-phase alkynyl amine compounds and product obtained by preparation method
  • Preparation method of water-phase alkynyl amine compounds and product obtained by preparation method
  • Preparation method of water-phase alkynyl amine compounds and product obtained by preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] To a pre-dried 4mL reaction flask, add benzyl-4-methylbenzenesulfonamide (53mg, 0.2mmol), copper sulfate pentahydrate (5mg, 0.02mmol), 1,10-phenanthroline ( 7.4mg, 0.04mmol), potassium carbonate (56.4mg, 0.4mmol), while adding 2wt.% surfactant APGS-550-M aqueous phase system (0.4mL), and finally adding phenylacetylene bromide (44.3mg, 0.24mmol) , after heating to 50°C, stirring was continued at 900-1000rpm for 26h.

[0037] After the reaction solution was stirred, it was extracted three times with ethyl acetate, and the organic phases extracted several times were combined into a 25mL eggplant-shaped flask, and the Heidolph rotary evaporator was used at a speed of 80-100rpm, a temperature of 38°C, and a vacuum of 0.1Mpa. , treated for 3 min, and then subjected to column chromatography using 200-mesh column chromatography silica gel, and the developer was petroleum ether: ethyl acetate = 20:1, and the target compound was isolated. (71mg, yield rate is 98%, an...

Embodiment 2

[0040]

[0041] To a pre-dried 4mL reaction flask, add N-benzyl-4-methoxybenzenesulfonamide (56.6mg, 0.2mmol), copper sulfate pentahydrate (5mg, 0.02mmol), 1,10-o- Phenanthroline (7.4mg, 0.04mmol), potassium carbonate (56.4mg, 0.4mmol), while adding 2wt.% surfactant APGS-550-M aqueous phase system (0.4mL), finally add phenylacetylene bromide (44.3mg , 0.24mmol), heated to 50°C, and continued to stir at 900-1000rpm for 26h.

[0042] After the reaction solution was stirred, it was extracted three times with ethyl acetate, and the organic phases extracted several times were combined into a 25mL eggplant-shaped flask, and the Heidolph rotary evaporator was used at a speed of 80-100rpm, a temperature of 38°C, and a vacuum of 0.1Mpa. , treated for 3 min, and then used 200 mesh column chromatography silica gel for column chromatography, and the developing solvent was petroleum ether: ethyl acetate = 15:1, and the target compound was isolated. (71 mg, the yield is 90%, and the pur...

Embodiment 3

[0045]

[0046] To a pre-dried 4mL reaction flask, N-(2-furylmethyl)-4-methylbenzenesulfonamide (53mg, 0.2mmol), copper sulfate pentahydrate (5mg, 0.02mmol), 1 , 10-phenanthroline (7.4mg, 0.04mmol), potassium carbonate (56.4mg, 0.4mmol), while adding 2wt.% surfactant APGS-550-M aqueous phase system (0.4mL), finally adding phenylacetylene Bromine (44.3mg, 0.24mmol), after heating to 50°C, continued stirring at 900-1000rpm for 26h.

[0047] After the reaction solution was stirred, it was extracted three times with ethyl acetate, and the organic phases extracted several times were combined into a 25mL eggplant-shaped flask, and the Heidolph rotary evaporator was used at a speed of 80-100rpm, a temperature of 38°C, and a vacuum of 0.1Mpa. , treated for 3 min, and then subjected to column chromatography using 200-mesh column chromatography silica gel, and the developer was petroleum ether: ethyl acetate = 20:1, and the target compound was isolated. (40mg, yield rate is 81%, and t...

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Abstract

The invention relates to a preparation method of alkynyl amine compounds and products obtained by the preparation method, and belongs to the technical field of chemical synthesis. The method comprisesthe following steps: adding a secondary amine compound, copper sulfate pentahydrate, 1,10-phenanthroline and potassium carbonate into a 4 mL reaction flask, adding 2 wt% a surfactant APGS-550-M aqueous phase system, adding alkynyl bromide, performing heating to 50 DEG C, performing continuous stirring at 900-1000 rpm for 26 h, performing extraction for three times by using ethyl acetate, performing rotary evaporation concentration, and performing separation by using silica gel column chromatography to obtain the products. The method provided by the invention can be used for derivation of natural products and synthesis of drug structures; and the method has the following advantages: 1) water is used for replacing an organic solvent, so that the environmental pollution is reduced; 2) the reaction temperature is reduced, and the energy consumption is reduced; and 3) byproducts are few and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for preparing an aqueous phase acetylenic amine compound and a product thereof. Background technique [0002] For the method of alkyne amine compounds, at present, the main synthesis method: metal-catalyzed coupling reaction. Most of the reactions require higher temperatures and the use of organic solvents, such as toluene and tetrahydrofuran, which are harmful to humans and the environment. As early as 1991, the American Chemical Society proposed the concept of "green chemistry", and then put forward twelve principles of "green chemistry". As we all know, in the field of organic synthesis, the organic solvents used by people have serious problems such as strong toxicity, refractory degradation, flammability and explosion, and climate change. Therefore, the inevitable solvent pollution problem needs to be solved, and a green and efficient alkyne a...

Claims

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Application Information

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IPC IPC(8): C07C311/16C07C311/29C07C311/17C07C303/40C07D307/52
CPCC07C311/16C07C311/29C07C311/17C07C303/40C07D307/52
Inventor 黄申林杨云琴孟祥太朱宝龙贾莹
Owner NANJING FORESTRY UNIV
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