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Synthesis method of photocatalytic tertiary amine compound

A technology of tertiary amine compounds and synthetic methods, applied in the preparation of organic compounds, preparation of amino compounds from amines, chemical instruments and methods, etc., can solve the problems of weak redox ability, limited application, high price, etc. Strong universality, easy operation and low toxicity

Active Publication Date: 2020-02-14
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This class of metals is not only expensive but also toxic, which limits the application of this reaction to a certain extent.
Therefore, chemists have also developed some non-metallic dye photosensitizers, but their redox ability is often weaker than that of metal complexes

Method used

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  • Synthesis method of photocatalytic tertiary amine compound
  • Synthesis method of photocatalytic tertiary amine compound
  • Synthesis method of photocatalytic tertiary amine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] Photosensitizer PS1 (11.5mg, 0.01mmol) and potassium acetate (39.3mg, 0.4mmol) were added to the Schlenk reaction tube, vacuumed and replaced with nitrogen three times, and then the formula 4-phenylstyrene (36mg, 0.2mmol) and three Ethylamine (40.5mg, 0.4mmol) was dissolved in tetrahydrofuran (2mL), added to the above reaction tube under the protection of nitrogen, and under the irradiation of 15W blue LED, stirred and reacted at 25°C for 12 hours. After the reaction was completed, the obtained 100-200 mesh column chromatography silica gel was added to the reaction solution and the solvent was distilled off under reduced pressure, and the obtained crude product was separated by silica gel column chromatography, and eluted with petroleum ether / ethyl acetate=8 / 1 as the eluent, TLC followed the elution process, collected the eluent containing the target product, combined the eluent and evaporated the solvent to obtain the pure product (31.5 mg). The material wa...

Embodiment 2

[0040]

[0041] Photosensitizer PS3 (12.0mg, 0.01mmol) and potassium acetate (39.3mg, 0.4mmol) were added into the Schlenk reaction tube, vacuumed and replaced with nitrogen three times, and then the formula 4-phenylstyrene (36mg, 0.2mmol) and three Ethylamine (40.5mg, 0.4mmol) was dissolved in tetrahydrofuran (2mL), added to the above reaction tube under the protection of nitrogen, and under the irradiation of 15W blue LED, stirred and reacted at 25°C for 12 hours. After the reaction was completed, the obtained 100-200 mesh column chromatography silica gel was added to the reaction solution and the solvent was distilled off under reduced pressure, and the obtained crude product was separated by silica gel column chromatography, and eluted with petroleum ether / ethyl acetate=8 / 1 as the eluent, TLC followed the elution process, collected the eluent containing the target product, combined the eluent and evaporated the solvent to obtain the pure product. The material was a colo...

Embodiment 3

[0044]

[0045] Photosensitizer PS5 (10.5mg, 0.01mmol) and potassium acetate (39.3mg, 0.4mmol) were added to the Schlenk reaction tube, vacuumed and changed for nitrogen three times, and then the formula 4-phenylstyrene (36mg, 0.2mmol) and three Ethylamine (40.5mg, 0.4mmol) was dissolved in tetrahydrofuran (2mL), added to the above reaction tube under the protection of nitrogen, and under the irradiation of 15W blue LED, stirred and reacted at 25°C for 12 hours. After the reaction was completed, the obtained 100-200 mesh column chromatography silica gel was added to the reaction solution and the solvent was distilled off under reduced pressure, and the obtained crude product was separated by silica gel column chromatography, and eluted with petroleum ether / ethyl acetate=8 / 1 as the eluent, TLC followed the elution process, collected the eluent containing the target product, combined the eluent and evaporated the solvent to obtain the pure product. The material was a colorles...

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Abstract

The invention discloses a synthesis method of a photocatalytic tertiary amine compound. The method is specifically carried out according to the steps of: adding a photosensitizer and an alkaline substance into a Schlenk reaction tube, in a nitrogen atmosphere, dissolving olefin shown as formula I, formula II or formula III and tertiary amine shown as formula IV in an organic solvent to obtain a mixed solution, adding the mixed solution into the above reaction tube, carrying out stirring reaction for 6-14h at 25DEG C under the irradiation of a light source, and performing aftertreatment on theobtained reaction solution to obtain an amine compound shown as formula V, formula VI or formula VII respectively; wherein the mole ratio of the photosensitizer, the alkaline substance, the olefin shown as formula I, formula II or formula III and the tertiary amine shown as formula IV is 0.05:1-2:1:1.5-2.5. The method disclosed by the invention can be used for synthesis of tertiary amine that is difficult to prepare by existing method; a cheap and easily available copper-based catalyst is employed to replace a noble metal catalyst, and the toxicity is low; and the method has the advantages ofmild reaction conditions, saving of energy consumption, high yield, strong substrate universality, simple operation and the like.

Description

[0001] (1) Technical field [0002] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing photocatalyzed tertiary amine compounds. [0003] (2) Background technology [0004] Tertiary amines have unique physiological activities, are the most important structural units in medicinal chemistry, and widely exist in various drug molecules, as shown in formulas 1-4. The classic methods for synthesizing tertiary amines mainly include N-alkylation reaction and reductive amination reaction. The synthesis of tertiary amines by these two methods often requires lengthy steps and cumbersome post-processing, which seriously hinders the process of new drug development. With the development of transition metal catalyzed reactions, people have established a variety of methods for the synthesis of amine compounds from the raw materials of sp2 hybrid systems, such as Buchwald-Hartwig amination, olefin hydroamination, etc., but the strate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/68C07C221/00C07D213/38C07C211/27C07C225/06C07C211/28C07C211/29C07B37/02
CPCC07C221/00C07D213/38C07C209/68C07B37/02C07C211/27C07C225/06C07C211/28C07C211/29Y02B20/00
Inventor 刘运奎鲍汉扬郑立孟
Owner ZHEJIANG UNIV OF TECH
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