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Preparation method of piperazine ethane sulfonic acid derivatives

A technology for piperazine ethanesulfonic acid and derivatives, which is applied in the field of preparation of piperazine ethanesulfonic acid derivatives, can solve the problems of difficult to obtain qualified products, difficult to industrialized large-scale production, low crude product content and the like, and achieves low inorganic salt content. , The effect of reducing production cost and high yield

Pending Publication Date: 2020-01-14
SUZHOU YACOO SCI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After the reaction, distill water under reduced pressure to obtain a viscous solid-liquid mixture, heat ethanol to disperse, adjust the pH to 5 with glacial acetic acid, and obtain the crude HEPES with a crude product content of about 70%. The crude product has a low content and a large amount of inorganic salts. The refining process It is easy to become oily, it is difficult to obtain qualified products, and it is difficult to industrialize large-scale production

Method used

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  • Preparation method of piperazine ethane sulfonic acid derivatives
  • Preparation method of piperazine ethane sulfonic acid derivatives
  • Preparation method of piperazine ethane sulfonic acid derivatives

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preparation example Construction

[0040] The invention provides a kind of preparation method of piperazineethanesulfonic acid derivative, comprises following equation:

[0041]

[0042] Include the following steps:

[0043] 1) Mix 1.2-2.2mol 2-hydroxyethylpiperazine, 1mol 2-chloroethylsulfonate sodium with 100-200mL water, stir evenly, raise the temperature to 70-90°C, stop heating until the system self-heats to 103 -105°C, heat to reflux for 20-60min;

[0044] 2) Cool the reaction solution to 50-70°C, add triethylamine to the reaction solution to adjust the pH to 7-8, boil with 1-2L absolute ethanol and 6-10g activated carbon, and filter while it is hot;

[0045] 3) Use glacial acetic acid to adjust the pH to 4-5, stir the filtrate, cool and crystallize, filter, and dry;

[0046] 4) Add 700-800mL of ethanol to dissolve the dried sample in step 3, heat to reflux, add 130-160mL of water, stir to dissolve, filter while it is hot, and cool and filter the filtrate to obtain 4-hydroxyethylpiperazineethanesulfo...

Embodiment 1

[0049] The preparation method of 4-hydroxyethylpiperazineethanesulfonic acid comprises the following steps:

[0050] 1) Mix 260g (2mol) 2-hydroxyethylpiperazine, 165g (0.94mol) sodium 2-chloroethylsulfonate with 120mL water, stir evenly, the reaction solution becomes clear, the pH is about 10, and the temperature is raised to 85°C , stop heating until the system self-heats to 103-105 ° C, heat and reflux for 30 minutes, the reaction is over, and the pH is about 8;

[0051] 2) Cool the reaction solution to 60°C, add triethylamine to the reaction solution to adjust the pH to 7-8, boil with 1.5L of absolute ethanol and 8g of activated carbon for 30min, and filter while hot;

[0052] 3) Use glacial acetic acid to adjust the pH of the filtrate to 5, stir the filtrate, cool to 5° C. to crystallize overnight, filter, and dry to obtain 310 g of crude product, which is tested by titration after drying, and the content is 95%;

[0053] 4) Add 750mL of ethanol to the sample obtained in ...

Embodiment 2

[0056] The preparation method of 4-hydroxyethylpiperazineethanesulfonic acid comprises the following steps:

[0057] 1) Mix 244.4g (1.88mol) of 2-hydroxyethylpiperazine, 165g (0.94mol) of sodium 2-chloroethylsulfonate with 125mL of water, stir evenly, the reaction solution becomes clear, the pH is about 10, and the temperature is raised to 80°C, stop heating until the system self-heats to 103-105°C, heat and reflux for 30 minutes, the reaction is over, and the pH is about 8;

[0058] 2) Cool the reaction solution to 60°C, add triethylamine to the reaction solution to adjust the pH to 7-8, boil with 1.6L absolute ethanol and 8g activated carbon for 30min, and filter while hot;

[0059] 3) Use glacial acetic acid to adjust the pH of the filtrate to 5, stir the filtrate, cool to 5° C. to crystallize overnight, filter, and dry; 327 g of crude product is obtained, and the content is 95% after drying and titration test;

[0060] 4) Add 800mL of ethanol to the dried sample in step 3...

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Abstract

The invention discloses two preparation methods of piperazine ethane sulfonic acid derivatives. In the early stage of feeding, the reaction is initiated by pre-heating, and heating is carried out after the system is self-heated to a certain degree by reaction, so as to effectively control side reaction of 2-hydroxyethyl piperazine and 2-chloroethane sulfonic acid sodium salt, so that the reactioncan be carried out relatively thoroughly. By reducing the way of adding NaOH solution, the generation of NaCl in the reaction system is reduced, and then triethylamine hydrochloride soluble in water and ethanol is formed by forming salt with triethylamine, which can be directly removed from the system, thus reducing the way of desalting using ion exchange resin; by directly adding the mixed solution of ethanol to the water of the original reaction system for recrystallization, and further using ethanol-water mixed solution in the amount of water added, recrystallization is performed, so as toeffectively reduce the residue of inorganic salts, and the final product has relatively high purity.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of piperazineethanesulfonic acid derivatives. Background technique [0002] 4-Hydroxyethylpiperazineethanesulfonic acid (HEPES) is a hydrogen ion buffer, which has good buffering capacity in the pH range of 6.8-8.2, and can control a constant pH range for a long time. The final concentration used is 10-50mmol / L, and the general culture medium contains 20mmol / L HEPES to achieve buffering capacity, and has no toxic effect on cells. [0003] The current literature about the HEPES synthesis method is to first synthesize the HEPES sodium salt, and then pass through the ion resin exchange purification method. The ion resin exchange purification method has the disadvantages of short ion resin life, frequent replacement, and a lot of production wastewater, which seriously pollutes the environment. At the same time, the yield of the HEPES product obtained ...

Claims

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Application Information

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IPC IPC(8): C07D295/088
CPCC07D295/088
Inventor 袁永坤
Owner SUZHOU YACOO SCI CO LTD
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