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Preparation method and application of N-alpha-beta-containing unsaturated ketone compound

A ketone compound, unsaturated technology, applied in the field of drug synthesis, can solve the problems of difficult purification, high production cost, cumbersome process, etc., and achieve the effect of simple post-processing purification, reduced preparation cost and high yield

Pending Publication Date: 2021-03-26
烟台共进医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the technology disclosed in CN109796399A, the preparation of unsaturated ketone compounds containing N-αβ needs to be reacted in an inert solvent under the action of a metal catalyst and an oxidant, and the crude product after the reaction needs to be separated by chromatography to obtain the product, and the process is cumbersome. High production cost, difficult purification and low yield

Method used

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  • Preparation method and application of N-alpha-beta-containing unsaturated ketone compound
  • Preparation method and application of N-alpha-beta-containing unsaturated ketone compound
  • Preparation method and application of N-alpha-beta-containing unsaturated ketone compound

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Experimental program
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Embodiment 1

[0025] (1)

[0026] The table of raw materials of table 1 embodiment 1 step (1)

[0027] materials Feeding amount M moles molar feed ratio Acetophenone 50g 120.15 0.416mol 1 DMF-DMA 77.4g 119.2 0.649mol 1.5

[0028] Mix acetophenone and DMF-DMA together according to the dosage in Table 1, heat up to the reflux point, and the reaction system turns yellow after 20 minutes, then cool down the reaction system to -10°C, precipitate solids, methyl tert-butyl ether Slurry to obtain a pure yellow solid. The product obtained after beating is 50-60g in total, and the yield has reached more than 80%.

[0029] (2)

[0030] The raw material table of table 2 embodiment 1 step (2)

[0031]

[0032] According to the raw material consumption in table 2, in Add water, then add nitroaniline, then add ferric chloride hydrate, stir overnight, solid precipitates, add water to quench, extract with EA, concentrate through the column, and beat with...

Embodiment 2

[0034] (1)

[0035] Table 3 The raw material list of embodiment 2 step (1)

[0036] materials Feeding amount M moles molar feed ratio Acetophenone 50g 120.15 0.416mol 1 DMF-DMA 77.4g 119.2 0.649mol 1.5

[0037] Mix acetophenone and DMF-DMA together according to the dosage in Table 3, heat up to the reflux point, the reaction system turns yellow after 20 minutes, cool down the reaction system to -10°C, precipitate solids, methyl tert-butyl ether Slurry to obtain a pure yellow solid. The product obtained after beating is 50-60g in total, and the yield has reached more than 80%.

[0038] (2)

[0039] The raw material table of table 4 embodiment 2 steps (2)

[0040]

[0041] According to the amount of raw materials in Table 4, the Add in water to dissolve, then add aniline, ferric chloride hydrate, the color becomes darker, stir overnight, a solid precipitates, add water to quench, extract with EA, concentrate through the colum...

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Abstract

The invention relates to a preparation method of an N-alpha-beta-containing unsaturated ketone compound. The preparation method comprises the steps of (1) mixing the components, and heating to reflux;(2) heating and refluxing until the reaction system turns yellow, cooling, and separating out a solid; and (3) pulping by using methyl tert-butyl ether to obtain a yellow solid product. According tothe preparation method of the N-alpha-beta-containing unsaturated ketone compound, a reaction solvent, a catalyst and an oxidant are not needed, so that the raw material cost is reduced, the post-treatment purification is simple, the yield is high, the operation is simple, and the preparation cost is reduced.

Description

technical field [0001] The invention relates to a preparation method and application of an N-αβ-unsaturated ketone compound, belonging to the technical field of drug synthesis. Background technique [0002] N-αβ-containing unsaturated ketone compounds play a key role in various inflammatory pathways, and inhibition of the formation of this compound can lead to systemic side effects. N-αβ unsaturated ketone compounds seem to be a good leader for drug development, and N-αβ unsaturated ketone compounds have good curative effect on peritonitis and sepsis without any side effects. N-αβ unsaturated ketone compound is an organic compound with multiple reaction sites, which can use the characteristics of multiple reaction sites to participate in the reaction to generate a variety of drug molecules with high biological activity. Compounds containing N-αβ unsaturated ketones are pharmacological A very important compound in research and a good lead for drug development. [0003] In t...

Claims

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Application Information

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IPC IPC(8): C07C221/00C07C225/16A61P29/00
CPCC07C221/00A61P29/00
Inventor 于腾飞王伟崔宁宁陈锦春
Owner 烟台共进医药科技有限公司
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