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A kind of synthetic method of 1h-3-pyrrolidone compound

A technology of pyrrolidone and synthesis method, which is applied in chemical instruments and methods, organic compound/hydride/coordination complex catalyst, chemical/physical process, etc., can solve the problem of increased cost, single structure of pyrrolidone, and low reaction rate. It is difficult to control the amplification of heat and other problems, so as to achieve the effect of simple production process, low emission and mild production process.

Active Publication Date: 2022-06-21
大连普莱瑞迪化学有限公司
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Problems solved by technology

According to literature records, the synthesis of such compounds is mostly obtained by hydrogenation and amination of γ-butyrolactone or maleic anhydride as raw materials, but these methods often synthesize pyrrolidone with a single structure, and further modification will greatly increase the cost
According to early literature reports, the synthesis method of 1H-3-pyrrolidone compounds can be synthesized by acylation and cyclization using enaminone as a raw material under the promotion of copper trifluoroacetate in trifluoroacetic acid solvent, and the reaction yield is about 85%. , but the cost of the catalytic system is high and it is difficult to realize industrialization. Another method for synthesizing 1-H-3-pyrrolidone compounds is relatively simple. The target product can be obtained by using acetylacetone and primary amine as raw materials under the catalysis of hydrogen peroxide , but the reaction rate is too fast and the heat release is serious, it is difficult to control its amplification, and the oxidation system produces more by-products, so it is not suitable for large-scale industrial production

Method used

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  • A kind of synthetic method of 1h-3-pyrrolidone compound
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  • A kind of synthetic method of 1h-3-pyrrolidone compound

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Experimental program
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Effect test

Embodiment 1

[0023] In a 250ml round-bottom flask, add acetylacetone (22.0g, 220mmol), benzylamine (10.7g, 100mmol), the complex formed by ferric chloride and 1,10-phenanthroline (3.0mmol), cuprous iodide ( 1.5mmol) and toluene (100ml). Turn on stirring and raise the temperature, and react at 105°C (105°C±2°C) for 8 hours, during which the bottle mouth is kept open. The temperature was stopped, and then 100 ml of deionized water was added. After the two phases were separated, the aqueous phase was extracted three times with ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, distillation under reduced pressure, the concentrate is separated by chromatographic column (the column filler is silica gel, and the elution is calculated as the ratio of petroleum ether and ethyl acetate is 5:1) or recrystallization separation (mixed solvent of acetone and ethyl acetate) , 21.1 g of colorless crystals were obtained, the yield was 85%, the pr...

Embodiment 2

[0025] In a 250ml round-bottomed flask, add acetylacetone (22.0g, 220mmol), n-butylamine (7.4g, 100mmol), the complex formed by iron nitrate and L-lysine (3.0mmol), cuprous iodide (1.5mmol) ) and toluene (100 ml). Turn on stirring and raise the temperature, and react at 105°C (105°C±2°C) for 8 hours, during which the bottle mouth is kept open. The temperature was stopped, and then 100 ml of deionized water was added. After the two phases were separated, the aqueous phase was extracted three times with ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, distillation under reduced pressure, the concentrate is separated by chromatographic column (the column filler is silica gel, and the elution is calculated as the ratio of petroleum ether and ethyl acetate is 5:1) or recrystallization separation (mixed solvent of acetone and ethyl acetate) , 15.1g of colorless crystals were obtained, the yield was 67%, the product purit...

Embodiment 3

[0027] In a 250ml round-bottomed flask, add acetylacetone (22.0g, 220mmol), n-butylamine (7.4g, 100mmol), the complex formed by ferric chloride and L-proline (3.0mmol), and copper oxide (1.5mmol) and DMSO (100ml). Turn on stirring and raise the temperature, and react at 105°C (105°C±2°C) for 8 hours, during which the bottle mouth is kept open. The temperature was stopped, and then 100 ml of deionized water was added. After the two phases were separated, the aqueous phase was extracted three times with ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, distillation under reduced pressure, the concentrate is separated by chromatographic column (the column filler is silica gel, and the elution is calculated as the ratio of petroleum ether and ethyl acetate is 5:1) or recrystallization separation (mixed solvent of acetone and ethyl acetate) , 15.1g of colorless crystals were obtained, the yield was 67%, the product purit...

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Abstract

The present invention provides a kind of synthetic method of 1H-3-pyrrolidone compound, take aliphatic primary amine and β-diketone compound as raw material, in organic solvent, mix evenly with iron complex catalyst and copper salt cocatalyst, in React at 40-110°C for 8-12 hours. After the reaction, separate and purify to obtain 1H-3-pyrrolidone compounds. The product synthesized by the method has a purity of over 99% (as determined by HPLC) after purification, and a yield of up to 85%. The production process is simple, the production process is mild and the emission is low, so the process design can be directly carried out on the basis of laboratory work, and the scale-up production can be realized.

Description

technical field [0001] The invention relates to the technical field of organic chemical industry, in particular to a method for preparing a fine chemical 1H-3-pyrrolidone compound, in particular to a method for synthesizing an important organic chemical intermediate 1H-3-pyrrolidone compound. Background technique [0002] The heterocyclic moiety of 1H-3-pyrrolidone is a common structure in natural products, pharmaceuticals and biologically active components, but there are not many methods for artificial synthesis of this structure. Most of the existing methods have harsh conditions, or the reaction process is difficult to control due to factors such as exothermic, resulting in hindered industrial scale-up. Therefore, it is of practical significance to develop a fast, mild, green and efficient method to construct this structural unit. According to literature records, the synthesis of such compounds is mostly obtained by hydroamination of γ-butyrolactone or maleic anhydride a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/36B01J31/30B01J31/28B01J31/22
CPCC07D207/36B01J31/30B01J31/28B01J31/183B01J31/2217B01J2531/842
Inventor 苏建龙温树清
Owner 大连普莱瑞迪化学有限公司
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