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Method for synthesizing aliphatic propargylamines

A technology for propargyl amine and compound, which is applied in the field of synthesizing aliphatic propargyl amine compounds, can solve the problems of unsuitability for large-scale industrial production, long reaction time and high reaction cost, and achieves easy subsequent separation and shortened reaction time. , the effect of simple raw materials

Inactive Publication Date: 2009-11-11
北京理工亘元科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, propargyl bromide and propargyl benzene sulfonate are not produced in China, and the price of raw materials is high, so the reaction cost is high, the reaction time is long, and the yield is low, so it is not suitable for large-scale industrial production.

Method used

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  • Method for synthesizing aliphatic propargylamines
  • Method for synthesizing aliphatic propargylamines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 0.025g CuI, 0.015mL hydrochloric acid and 5mL dimethyl sulfoxide to a 50mL three-neck flask equipped with a stirrer, thermometer, and gas outlet, respectively, pass acetylene gas into the flask, react at 65°C for 1h, and cool to room temperature after the reaction stops. Add dropwise 0.0033mol 2-heptylamine and 0.005mol formaldehyde to the reaction system, react for 5h, track the reaction with thin-layer chromatography, adjust the pH of the solution to 10 with NaOH solution after the reaction, let it stand, extract with ether, and separate the water phase. Extract the organic layer with a phosphate buffer solution with a pH value of 3.5, separate the organic phase, adjust the aqueous phase to pH = 10 with NaOH solution, extract with ether, separate the aqueous phase, and evaporate the organic phase to dryness under reduced pressure to obtain N-alkyne Propyl-2-heptylamine 0.23g, yield 46%.

[0023] 1H NMR (CDCl3, 300MHz) δ: 3.49(q; 2H; propynyl CH 2 -; J=9.37Hz), 2....

Embodiment 2

[0027] Add 0.025gCuI, 0.015mL hydrochloric acid and 15mL dimethyl sulfoxide to a 50mL three-neck flask equipped with a stirrer, a thermometer and a gas outlet, respectively, pass acetylene gas into the flask, and react at room temperature for 2h. After the reaction stops, cool to room temperature, respectively. Add dropwise 0.0033mol 2-heptylamine and 0.0165mol formaldehyde to the reaction system, react for 5 hours, track the reaction with thin-layer chromatography, adjust the pH of the solution to 10 with NaOH solution after the reaction, let stand, extract with ether, separate the water phase, and use Extract the organic layer with a phosphate buffer solution with a pH value of 4.0, separate the organic phase, adjust the aqueous phase to pH = 10 with NaOH solution, extract with ether, separate the aqueous phase, and evaporate the organic phase to dryness under reduced pressure to obtain N-propargyl Base-2-heptylamine 0.3g, yield 61%.

[0028] 1H NMR (CDCl3, 300MHz) δ: 3.49(q...

Embodiment 3

[0030] Add 0.05g CuI, 0.03mL hydrochloric acid and 5mL dimethyl sulfoxide to a 50mL three-neck flask equipped with a stirrer, thermometer and gas outlet respectively, pass acetylene gas into the flask, react at 65°C for 1h, cool to room temperature after the reaction stops, Add dropwise 0.0033mol 2-heptylamine and 0.005mol formaldehyde to the reaction system, react for 10h, track the reaction with thin-layer chromatography, adjust the pH of the solution to 10 with NaOH solution after the reaction, let stand, extract with ether, and separate the water phase. Extract the organic layer with a phosphate buffer solution with a pH value of 4.0, separate the organic phase, adjust the aqueous phase to pH = 11 with NaOH solution, extract with ether, separate the aqueous phase, and evaporate the organic phase to dryness under reduced pressure to obtain N-alkyne Propyl-2-heptylamine 0.43g, yield 86%.

[0031] 1H NMR (CDCl3, 300MHz) δ: 3.49(q; 2H; propynyl CH 2 -; J=9.37Hz), 2.85(q; 1H; ...

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Abstract

The invention relates to a method for synthesizing aliphatic propargylamines, belonging to the field of the synthesis of aliphatic compounds. The method comprises the following steps: acetylene, aliphatic amine and formaldehyde are synthesized into the aliphatic propargylamines under normal pressure and a certain temperature according to a certain proportion, DMSO or N, N-DMF is used as a reactive solvent, cupric salt is used as a catalyst, and hydrochloric acid is used as a cocatalyst, wherein the cupric salt catalyst is one of cuprous chloride, cuprous bromide, cuprous iodide, cuprous oxide, cupric chloride, cupric bromide and cupric sulfate; the cocatalyst is the hydrochloric acid; the solvent is the DMSO or the N, N-DMF; and the aliphatic amine contains 3 to 30 carbon atoms. The invention has the advantages of low reaction cost, high yield, little side reactions, low difficulty of a reaction technology, simple operation, easy subsequent-separation operation of a product, reaction time shortening and obvious enhancement of the economical efficiency.

Description

technical field [0001] The invention relates to a method for synthesizing aliphatic propargylamine compounds, which belongs to the field of synthesis of aliphatic compounds. technical background [0002] Aliphatic propargyl amine compounds are an important class of compounds, which have been widely used in medicine, pesticides and other fields. At present, the aliphatic propargyl amine compounds are obtained by the substitution reaction of aliphatic amines and propargyl donors. Existing needs to adopt expensive propargyl bromide or propargyl benzene sulfonate as propargyl donor and aliphatic amine reaction 24 hours to obtain the report of aliphatic propargyl amine compound (patent No. is US 0159393 and US 0159393 and US 6809120 patent report). However, propargyl bromide and propargyl benzenesulfonate are not produced in China, and the price of raw materials is high, so the reaction cost is high, the reaction time is long, and the yield is low, so they are not suitable for ...

Claims

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Application Information

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IPC IPC(8): C07C209/24C07C209/60C07C211/03
Inventor 邓玉林戴荣继杨林刘伟孟薇薇张信生
Owner 北京理工亘元科技有限公司
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