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Synthesis method of 1H-3-pyrrolidone compound

A technology for pyrrolidone and synthetic methods, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve the problems of increased cost, single structure of pyrrolidone, slow reaction rate It is difficult to control the amplification of heat, and achieve the effect of low emission, mild production process and simple production process

Active Publication Date: 2020-07-17
大连普莱瑞迪化学有限公司
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  • Abstract
  • Description
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  • Application Information

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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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  • Synthesis method of 1H-3-pyrrolidone compound
  • Synthesis method of 1H-3-pyrrolidone compound
  • Synthesis method of 1H-3-pyrrolidone compound

Examples

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 (3.0mmol) that iron chloride and 1,10-phenanthroline form, cuprous iodide ( 1.5mmol) and toluene (100ml). Turn on the stirring and raise the temperature, and react at 105°C (105°C±2°C) for 8 hours, keeping the bottle mouth open during the reaction. Stop heating, then add 100ml of deionized water, after the two phases are separated, the aqueous phase is extracted three times with ethyl acetate, the organic phases are combined, and dried with anhydrous sodium sulfate. After filtration, distillation under reduced pressure, the concentrate is separated by chromatographic column (the filler of chromatographic column is silica gel, and the ratio of petroleum ether and ethyl acetate is 5:1 for elution) or recrystallization separation (mixed solvent of acetone and ethyl acetate) , 21.1 g of colorless crystals were obtained, the yield was 85%, and the product purity was ...

Embodiment 2

[0025] In a 250ml round bottom flask, add acetylacetone (22.0g, 220mmol), n-butylamine (7.4g, 100mmol), the complex (3.0mmol) formed by iron nitrate and L-lysine, cuprous iodide (1.5mmol ) and toluene (100ml). Turn on the stirring and raise the temperature, and react at 105°C (105°C±2°C) for 8 hours, keeping the bottle mouth open during the reaction. Stop heating, then add 100ml of deionized water, after the two phases are separated, the aqueous phase is extracted three times with ethyl acetate, the organic phases are combined, and dried with anhydrous sodium sulfate. After filtration, distillation under reduced pressure, the concentrate is separated by chromatographic column (the filler of chromatographic column is silica gel, and the ratio of petroleum ether and ethyl acetate is 5:1 for elution) or recrystallization separation (mixed solvent of acetone and ethyl acetate) , 15.1 g of colorless crystals were obtained, the yield was 67%, the product purity was ≥99% (as determi...

Embodiment 3

[0027] In a 250ml round bottom flask, add acetylacetone (22.0g, 220mmol), n-butylamine (7.4g, 100mmol), the complex (3.0mmol) formed by ferric chloride and L-proline, copper oxide (1.5mmol) and DMSO (100ml). Turn on the stirring and raise the temperature, and react at 105°C (105°C±2°C) for 8 hours, keeping the bottle mouth open during the reaction. Stop heating, then add 100ml of deionized water, after the two phases are separated, the aqueous phase is extracted three times with ethyl acetate, the organic phases are combined, and dried with anhydrous sodium sulfate. After filtration, distillation under reduced pressure, the concentrate is separated by chromatographic column (the filler of chromatographic column is silica gel, and the ratio of petroleum ether and ethyl acetate is 5:1 for elution) or recrystallization separation (mixed solvent of acetone and ethyl acetate) , 15.1 g of colorless crystals were obtained, the yield was 67%, the product purity was ≥99% (as determine...

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Abstract

The invention provides a synthetic method of a 1H-3-pyrrolidone compound. The method comprises the following steps: taking aliphatic primary amine and a beta-diketone compound as raw materials, uniformly mixing the raw materials with an iron complex catalyst and a copper salt cocatalyst in an organic solvent, reacting at 40-110 DEG C for 8-12 hours, and separating and purifying after the reactionis finished, thereby obtaining the 1H-3-pyrrolidone compound. After purification, the purity of the product synthesized by the method can reach 99% or above (determined by HPLC), and the yield can reach 85%. And the production process is simple, the production process is mild, and the discharge amount is low, so that the process design can be directly carried out on the basis of laboratory work, and large-scale production is realized.

Description

technical field [0001] The invention relates to the technical field of organic chemical industry, in particular to a preparation method of fine chemical 1H-3-pyrrolidone compounds, in particular to a synthesis method of important organic chemical intermediates 1H-3-pyrrolidone compounds. Background technique [0002] The heterocyclic moiety of 1H-3-pyrrolidone compound is a common structure in natural products, drugs and bioactive components. However, there are not many methods for artificially synthesizing this structure. Most of the existing methods have harsh conditions, or the reaction process is difficult to control due to factors such as heat release, which hinders industrial scale-up. Therefore, it is of great practical significance to develop a quick, mild, green and efficient method to construct this structural unit. According to literature records, the synthesis of such compounds is mostly obtained by hydrogenation and amination of γ-butyrolactone or maleic anhydr...

Claims

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Application Information

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Patent Type & Authority Applications(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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