Method for preparing tranexamic acid

A technology of tranexamic acid and methanol is applied in the field of preparation of tranexamic acid, and achieves the effects of high yield, simple operation, cheap and easily available raw materials

Active Publication Date: 2019-08-23
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The purpose of the present invention is to solve the deficiencies of the existing tranexamic acid preparation methods, and provide a method for preparing tranexamic acid with cheap and easy-to-obtain raw materials and high yield, which is suitable for industrial production

Method used

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  • Method for preparing tranexamic acid
  • Method for preparing tranexamic acid
  • Method for preparing tranexamic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] 1) Add 288.4g (2mol) of 1,4-cyclohexanedimethanol (cis-trans mixed) and 608.4g of hydrochloric acid (6mol) with a mass fraction of 36% to the reactor, and stir the reaction at 85°C for 12h. After the reaction, cool to room temperature, add 300g of toluene for extraction, and wash with water until neutral. Concentrated under reduced pressure to obtain 257.6g of 4-chloromethylcyclohexylmethanol (cis-trans mixed), GC purity 91.7%, yield 79.2%;

[0049] 2) Add 81.3g (0.5mol) 4-chloromethylcyclohexylmethanol (cis-trans mixed) and 500g trifluoroacetic acid to the reactor, add 69g (1mol) sodium nitrite under stirring at 0°C in an oxygen atmosphere, Then rise to 25 ℃ for 6h. Add 300g of dichloromethane after concentrating under reduced pressure, adjust to neutral with 5% sodium bicarbonate solution, separate the water phase, and concentrate the organic phase under reduced pressure to obtain 86.6g of 4-chloromethylcyclohexyl formic acid (cis and trans mixed), GC Purity 90.8%, ...

Embodiment 2

[0052] 1) Add 288.4g (2mol) trans-1,4-cyclohexanedimethanol and 608.4g hydrochloric acid (6mol) with a mass fraction of 36% to the reactor, and stir at 90°C for 10h. After the reaction, cool to room temperature, add 300g of toluene for extraction, and wash with water until neutral. Concentrated under reduced pressure to obtain 259.3 g of trans-4-chloromethylcyclohexylmethanol with a GC purity of 92.1% and a yield of 79.7%;

[0053] 2) Add 81.3g (0.5mol) trans-4-chloromethylcyclohexylmethanol and 500g trifluoroacetic acid to the reactor, add 69g (1mol) under stirring at 0°C in an air atmosphere with an oxygen content of 21% Sodium nitrite, then rose to 30 ° C for 5h. After concentration under reduced pressure, 300 g of dichloromethane was added, adjusted to neutral with 5% sodium bicarbonate solution, the water phase was separated, and the organic phase was concentrated under reduced pressure to obtain 86.8 g of trans-4-chloromethylcyclohexylcarboxylic acid, GC purity 91.5%, ...

Embodiment 3

[0058] 1) Add 288.4g (2mol) of 1,4-cyclohexanedimethanol (cis-trans mixed) and 1088.6g of hydriodic acid (4mol) with a mass fraction of 47% into the reactor, and stir the reaction at 80°C for 8h. After the reaction, cool to room temperature, add 500g of toluene for extraction, and wash with water until neutral. Concentrate under reduced pressure to obtain 385.7 g of 4-iodomethylcyclohexylmethanol (cis-trans mixed), GC purity 91.2%, yield 75.9%.

[0059] 2) Add 127.1g (0.5mol) 4-iodomethylcyclohexylmethanol (cis-trans mixed) and 500g trifluoroacetic acid into the reactor, add 69g (1mol) sodium nitrite under stirring at 0°C in an oxygen atmosphere, Then it was raised to 25°C for 5h. After concentrating under reduced pressure, add 300g of dichloromethane, adjust to neutral with 5% sodium bicarbonate solution, separate the water phase, and concentrate the organic phase under reduced pressure to obtain 130.9g of 4-iodomethylcyclohexylcarboxylic acid (cis and reverse mixed), GC pu...

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Abstract

The invention relates to a method for preparing tranexamic acid. The method comprises the following steps: reacting 1,4-cyclohexanedimethanol, used as starting material, with an HX acid to generate 4-chloromethylcyclohexylmethanol or 4-iodomethylcyclohexylmethanol, carrying out an oxidation reaction in an atmosphere of a gas containing 21-100% of oxygen in order to produce 4-chloromethylcyclohexylcarboxylic acid or 4-iodomethylcyclohexylcarboxylic acid, carrying out an aminolysis reaction in an autoclave, introducing liquid ammonia or ammonia water having an ammonia content of 15-28% to the aminolysis reaction system, and transforming the obtained reaction product with an alkali after the aminolysis reaction is finished in order to obtain the tranexamic acid, wherein X is Cl or I. Comparedwith the prior art, the preparation method has the advantages of cheap and easily available raw materials and low cost. The method also has the advantages of simplicity in operation, high yield, andsuitableness for industrial production.

Description

technical field [0001] The invention relates to a preparation method of tranexamic acid, which belongs to the technical field of drug synthesis. Background technique [0002] The chemical name of tranexamic acid is trans-4-aminomethylcyclohexanecarboxylic acid (Tranexamic acid), also known as tranexamic acid. It has significant anti-fibrinolytic activity, can stabilize fibrin, and is an effective hemostatic agent for bleeding caused by blood coagulation factors, platelets, vascular factors and tissue factor disorders. It has been widely used in clinical practice in China and is listed in the new Chinese Pharmacopoeia load. The hemostatic effect is only effective for the trans-form, while the cis-form is almost ineffective, and the former is about 50 times stronger than the latter. [0003] There are many preparation methods of tranexamic acid reported at home and abroad, mainly the following: [0004] 1. Methyl acrylate method [0005] Using methyl acrylate and chlorobut...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/30C07C229/46C07C227/08C07C227/32C07C29/62C07C31/44
CPCC07C227/30C07C227/08C07C51/235C07C29/62C07C227/32C07C2601/14C07B2200/07C07C229/46C07C61/15C07C31/44
Inventor 刘忠文王斌贾公明周银波王宁
Owner VALIANT CO LTD
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