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Synthesis method of 1-teriary butoxy carbonyl-4-piperidone

A technology of tert-butoxycarbonyl and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of backward production process, low yield, low purity of 1-tert-butoxycarbonyl-4-piperidone, etc., and reduce energy consumption. , the effect of reducing production costs

Inactive Publication Date: 2012-06-27
兰州博实生化科技有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the current domestic process for synthesizing 4-piperidone is to use ethyl acrylate as a raw material, ethanol as a solvent, heating and refluxing, closing the ring with sodium alkoxide, and passing hydrogen chloride gas to make salt. The industrialization method is relatively low, and the production process is backward.
Cause the productive rate of this synthesis process to be low, the purity of the synthetic 1-tert-butoxycarbonyl-4-piperidone is lower, and energy consumption is big, and raw material cost is too high, and pollution is more serious

Method used

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  • Synthesis method of 1-teriary butoxy carbonyl-4-piperidone
  • Synthesis method of 1-teriary butoxy carbonyl-4-piperidone
  • Synthesis method of 1-teriary butoxy carbonyl-4-piperidone

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Embodiment 1

[0033] According to the molar ratio of 1:2, benzylamine and methyl acrylate were taken respectively, methyl acrylate and benzylamine were dissolved in methanol, and Michael addition reaction was carried out at room temperature for 10 hours, and then, the product of the reaction was purified by the existing method, After the purification is completed, methanol is distilled off at a temperature of 40° C. to obtain piperidone intermediate 1; according to a molar ratio of 1.2:1, metal sodium and prepared piperidone intermediate 1 are respectively taken, and piperidone intermediate 1 is prepared. Dissolve metal sodium in toluene, conduct Dickmann condensation reaction at 100°C for 2 hours, purify the product, and obtain piperidone intermediate 2; the molar ratio is 6:1, and the concentration is 5mol / L Concentrated hydrochloric acid and the obtained piperidone intermediate 2 were decarboxylated at 80°C for 4 hours to obtain the crude product 1-benzyl-4-piperidone hydrochloride; and ...

Embodiment 2

[0038] According to the molar ratio of 1:2.5, take benzylamine and methyl acrylate respectively, dissolve methyl acrylate and benzylamine in methanol, carry out Michael addition reaction at room temperature for 16 hours, then purify the reaction product by using existing methods, purify After completion, methanol was distilled off at a temperature of 60° C. to obtain piperidone intermediate 1; according to a molar ratio of 2:1, metal sodium and prepared piperidone intermediate 1 were respectively taken, and piperidone intermediate 1 was prepared. Dissolve metal sodium in toluene, and conduct a Dickmann condensation reaction at 125°C for 3 hours, then purify the product to obtain piperidone intermediate 2; the molar ratio is 12:1, and the concentration is taken separately Concentrated hydrochloric acid of 7 mol / L and the prepared piperidone intermediate 2, decarboxylation reaction at 100°C for 8 hours to obtain crude product 1-benzyl-4-piperidone hydrochloride; volume ratio 1:3 ...

Embodiment 3

[0040] According to the molar ratio of 1:2.25, benzylamine and methyl acrylate were taken respectively, methyl acrylate and benzylamine were dissolved in methanol, and Michael addition reaction was carried out at room temperature for 13 hours, and then, the product of the reaction was purified by the existing method, After the purification is completed, methanol is distilled off at a temperature of 50° C. to obtain piperidone intermediate 1; according to a molar ratio of 1.6:1, metal sodium and prepared piperidone intermediate 1 are respectively taken, and piperidone intermediate 1 and metal sodium were dissolved in toluene, and at a temperature of 112.5°C, Dickmann condensation reaction was carried out for 2.5 hours, and then, the product was purified to obtain piperidone intermediate 2; the molar ratio was 9:1, and the concentration was respectively Concentrated hydrochloric acid of 6mol / L and the prepared piperidone intermediate 2, decarboxylation reaction at 90°C for 6 hour...

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Abstract

The invention relates to a synthesis method of 1-teriary butoxy carbonyl-4-piperidone. The synthesis method comprises the following steps: dissolving benzylammine and methyl acrylate with methyl alcohol to carry out Michael addition reaction at room temperature, removing the methyl alcohol, and then obtaining piperidine intermediate 1; dissolving the piperidine intermediate1 and sodium in tolueneto carry out Diekman condensation reaction at high temperature, and then obtaining piperidone intermediate 2; carrying out decarboxyl reaction on the piperidone intermediate 2 and concentrated hydrochloric acid, and then obtaining crude 1-benzyl-4-piperidone hydrochloride; dissolving with ethanol solution, crystallizing, and then obtaining fine 1-benzyl-4-piperidone hydrochloride; adding a catalyst and the fine 1-benzyl-4-piperidone hydrochloride in the concentrated hydrochloric acid, and then preparing 4-piperidone hydrochloride; and reacting triethylamine, di-tert-butyl dicarbonate with the4-piperidone hydrochloride at room temperature to obtain a reaction product; and recrystallizing the reaction product and then preparing the 1-teriary butoxy carbonyl-4-piperidone. The synthesis method in the invention is simple and convenient in process, and the prepared product has the advantages of high purity and low energy consumption.

Description

technical field [0001] The invention belongs to the technical field of biomedicine and relates to a method for synthesizing a drug intermediate, in particular to a method for synthesizing 1-tert-butoxycarbonyl-4-piperidone. Background technique [0002] 1-tert-butoxycarbonyl-4-piperidone is a very important intermediate of medicine, pesticide and other chemical additives. my country's annual demand is about 80 tons, of which about 55 tons depend on imports, and there is still a market gap of nearly 20 tons every year. However, the current domestic process for synthesizing 4-piperidone is to use ethyl acrylate as a raw material, ethanol as a solvent, heating to reflux, closing the ring with sodium alkoxide, and making salt through hydrogen chloride gas. The industrialization method is relatively low, and the production process is backward. As a result, the yield of the synthesis process is low, the purity of the synthesized 1-tert-butoxycarbonyl-4-piperidone is low, and the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/74
Inventor 李建东
Owner 兰州博实生化科技有限责任公司
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