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Preparation method of ligustrazine

A technology of ligustrazine and solution, applied in the field of compound preparation, can solve the problems of low yield, long reaction time, large energy consumption, etc., and achieve the effects of strong stability, reduction of processing steps and energy saving

Active Publication Date: 2015-02-25
HEFEI PINGGUANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] 3. Patent CN200610054510.2 provides a preparation method of ligustrazine, using 3-hydroxy-2-butanone, ammonium acetate and ethanol as raw materials, N 2 Protection, using manganese dioxide or copper oxide as an oxidant, post-processing to obtain the product through two vacuum distillations, long reaction time, large energy consumption, and yield less than 72%

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  • Preparation method of ligustrazine
  • Preparation method of ligustrazine

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Embodiment 1

[0042] The preparation method of a kind of ligustrazine proposed by the present invention comprises the following steps:

[0043]S1, 21 parts of 3-hydroxy-2-butanone and 19 parts of ammonium acetate are added to the reaction vessel as main ingredients by weight, after adding dehydrated alcohol, feed nitrogen, and the temperature that the water bath is heated to the main ingredient is 89 ° C After stirring for 5h, stop feeding nitrogen gas until the temperature is lowered to room temperature, wherein the volume-to-weight ratio (ml:g) of absolute ethanol and 3-hydroxy-2-butanone is 3.2:1;

[0044] S2, add aromatization catalyst and glacial acetic acid in reaction vessel and stir for 1h, then filter to obtain filtrate A, wherein the weight ratio of aromatization catalyst and main material is 38.5:38, and aromatization catalyst is composed of potassium bromate and hydrogen sulfite The molar ratio of sodium is 1.2:0.9, and the volume-to-weight ratio of glacial acetic acid and potas...

Embodiment 2

[0051] The preparation method of a kind of ligustrazine proposed by the present invention comprises the following steps:

[0052] S1, add 19.7 parts of 3-hydroxy-2-butanone and 20.2 parts of ammonium acetate as main ingredients into the reaction vessel by weight, add dehydrated ethanol, feed nitrogen, and heat the water bath to the temperature of the main ingredients to be 80 ° C After stirring for 7h, stop feeding nitrogen gas until the temperature is lowered to room temperature, wherein the volume-to-weight ratio (ml:g) of absolute ethanol and 3-hydroxy-2-butanone is 2.9:1;

[0053] S2, add aromatization catalyst and glacial acetic acid to the reaction vessel and stir for 1.7h, then filter to obtain filtrate A, wherein the weight ratio of aromatization catalyst and main material is 36.5:41, and aromatization catalyst is composed of potassium bromate and sulfurous acid The molar ratio of sodium hydrogen is 0.9:1.2, and the volume-to-weight ratio of glacial acetic acid and pot...

Embodiment 3

[0060] The preparation method of a kind of ligustrazine proposed by the present invention comprises the following steps:

[0061] S1, add 20.3 parts of 3-hydroxy-2-butanone and 19.5 parts of ammonium acetate as main ingredients to the reaction vessel by weight, add dehydrated alcohol, feed nitrogen, and heat the water bath to the temperature of the main ingredients to be 82 ° C After stirring for 6h, stop feeding nitrogen gas until the temperature drops to room temperature, wherein the volume-to-weight ratio (ml:g) of absolute ethanol and 3-hydroxy-2-butanone is 3.1:1;

[0062] S2, add aromatization catalyst and glacial acetic acid in reaction vessel and stir for 2h, then filter to obtain filtrate A, wherein the weight ratio of aromatization catalyst and main material is 35.5:42, and aromatization catalyst is composed of potassium bromate and hydrogen sulfite The molar ratio of sodium is 0.8:1.3, and the volume-to-weight ratio of glacial acetic acid and potassium bromate is (m...

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Abstract

The invention discloses a preparation method of ligustrazine, wherein the preparation method comprises the following steps: adding 3-hydroxy-2-butanone and ammonium acetate as main materials into a reaction vessel, then adding anhydrous ethanol, introducing nitrogen, carrying out water bath heating on the reaction vessel, stirring, stropping introduction of the nitrogen, and waiting the temperature to be dropped to room temperature; adding an aromatization catalyst, then stirring, and filtering to obtain a filtrate A; concentrating the filtrate A to obtain a solution B; adding water and an extraction agent into the B solution, extracting, and taking an upper-layer solution to obtain a solution C; carrying out reduced pressure distillation on the solution C to obtain a solution D; adding water into the solution D, and carrying out cooling crystallization to obtain a mixed material E; and filtering the mixed material E to obtain ligustrazine crystals. The reaction time is greatly shortened, the purification processing is more convenient, the method has the advantages of energy conservation and environmental protection, the prepared ligustrazine is in a needle-shaped crystal form, and the yield can reach 87%.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to a preparation method of ligustrazine. Background technique [0002] Ligustrazine is an alkaloid obtained by separation and purification from the rhizome of Ligusticum chuanxiong, a plant belonging to the genus Umbelliferae. Its chemical name is 2,3,5,6-tetramethylpyrazine, or tetramethylpyrazine for short. It has relatively good pharmacological effects such as dilating blood vessels, mildly reducing blood pressure, inhibiting platelet adhesion and aggregation and thrombosis, and inhibiting the proliferation of smooth muscle cells and fibroblasts. Now it is mainly used in clinical treatment of occlusive vascular diseases, such as cerebral embolism, coronary heart disease, angina pectoris, vasculitis, chronic pulmonary heart disease, chronic renal failure, etc. [0003] Ligustrazine is a colorless needle crystal with a molecular weight of 138.20. The melting point is...

Claims

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Application Information

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IPC IPC(8): C07D241/12
CPCC07D241/12
Inventor 王康林吕宾张成栋
Owner HEFEI PINGGUANG PHARMA
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