Tranexamic acid and preparation method thereof

A technology of tranexamic acid and p-toluic acid, which is applied in the direction of carboxylate preparation, cyanide reaction preparation, chemical instruments and methods, etc., can solve the problems of high raw material prices, unfavorable market promotion, and tranexamic acid yield Low-level problems, to achieve high yield and reduce production costs

Inactive Publication Date: 2020-08-25
安徽鼎旺医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The yield of tranexamic acid prepared by the existing tranexamic acid preparation process is low, and the raw material price used in the preparation of tranexamic acid is high, which greatly increases the preparation cost of tranexamic acid, which is not conducive to market promotion

Method used

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  • Tranexamic acid and preparation method thereof
  • Tranexamic acid and preparation method thereof
  • Tranexamic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A kind of tranexamic acid is made by following steps:

[0037] Step S1: Add magnesium powder, iodine powder, and tetrahydrofuran into the reaction kettle, and use nitrogen for protection. Under the conditions of rotation speed of 100r / min and temperature of 155°C, p-bromotoluene is added dropwise, and reflux reaction is carried out for 1h. Introduce carbon dioxide until the reactor is full, and react for 30 minutes at a temperature of 3° C., add hydrochloric acid solution, and react for 1 hour to obtain p-toluic acid;

[0038] Step S2: Add the p-toluic acid, N-bromosuccinimide, and carbon tetrachloride prepared in step S1 into the reaction kettle, and stir until the toluic acid is After completely dissolving with N-bromosuccinimide, add dibenzoyl peroxide, and carry out a reflux reaction at a temperature of 80°C for 2 hours to obtain intermediate 1;

[0039] Step S3: Add sodium carbonate and deionized water into the reaction kettle, and stir at a speed of 200r / min unti...

Embodiment 2

[0043] A kind of tranexamic acid is made by following steps:

[0044] Step S1: Add magnesium powder, iodine powder, and tetrahydrofuran into the reaction kettle, and use nitrogen to protect it. Under the conditions of rotation speed of 150r / min and temperature of 158°C, p-bromotoluene is added dropwise, and reflux reaction is carried out for 1.5h , feed carbon dioxide to fill the reactor, and react at a temperature of 4°C for 35 minutes, add hydrochloric acid solution, and react for 1.3 hours to obtain p-toluic acid;

[0045]Step S2: Add the p-toluic acid, N-bromosuccinimide, and carbon tetrachloride prepared in step S1 into the reaction kettle, and stir until the toluic acid is After completely dissolving with N-bromosuccinimide, add dibenzoyl peroxide, and carry out a reflux reaction at a temperature of 85°C for 3 hours to obtain intermediate 1;

[0046] Step S3: Add sodium carbonate and deionized water into the reaction kettle, and stir at a speed of 250r / min until the sod...

Embodiment 3

[0050] A kind of tranexamic acid is made by following steps:

[0051] Step S1: Add magnesium powder, iodine powder, and tetrahydrofuran into the reaction kettle, and protect it with nitrogen gas. Under the conditions of rotation speed of 200r / min and temperature of 160°C, p-bromotoluene is added dropwise, and reflux reaction is carried out for 2 hours. Introduce carbon dioxide until the reactor is full, and react for 40 minutes at a temperature of 5°C, add hydrochloric acid solution, and react for 1.5 hours to obtain p-toluic acid;

[0052] Step S2: Add the p-toluic acid, N-bromosuccinimide, and carbon tetrachloride prepared in step S1 into the reaction kettle, and stir until the toluic acid is After completely dissolving with N-bromosuccinimide, add dibenzoyl peroxide, and carry out a reflux reaction at a temperature of 90°C for 4 hours to obtain intermediate 1;

[0053] Step S3: Add sodium carbonate and deionized water into the reaction kettle, and stir at a speed of 300r / m...

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Abstract

The invention discloses tranexamic acid and a preparation method thereof. P-bromotoluene used as a raw material is prepared into a Grignard reagent; the Grignard reagent is further subjected to addition reaction with carbon dioxide, and the reaction product is hydrolyzed under an acidic condition to obtain p-toluic acid; bromine substitution reaction is carried out on p-toluic acid and N-bromosuccinimide to obtain an intermediate 1; phase transfer catalytic reaction is carried out on the intermediate 1 to obtain an intermediate 2; the intermediate 2 reacts with a saturated toluene solution ofammonia gas to replace an alcoholic hydroxyl group on the intermediate 2 with an amino group to obtain an intermediate 3; and the intermediate 3 and hydrogen are hydrogenated under the action of a supported nickel catalyst to obtain tranexamic acid. The yield of tranexamic acid prepared by the preparation method of tranexamic acid is high, and compared with an existing preparation method, most ofthe used raw materials are low-price raw materials, so that the production cost of tranexamic acid is greatly reduced.

Description

technical field [0001] The invention belongs to the technical field of chemical and pharmaceutical preparation, and in particular relates to tranexamic acid and a preparation method thereof. Background technique [0002] Tranexamic acid: also known as tranexamic acid, compared with the traditional hemostatic drug tranexamic acid, tranexamic acid has the following advantages14: ①Wide range of hemostasis, rapid effect, less side effects, and various clinical dosage forms (such as small volume injection, Large-capacity injections, tablets, freeze-dried powder injections, etc.) are quite convenient to use, ② Wide range of uses Not only widely used as first-line hemostatic drugs in various departments in clinical practice, but also more widely used in daily life as daily chemical products such as skin care products, toothpaste Wait. It is of great significance to carry out the deepening research of the technology of this product, which can not only create good economic benefits,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/16C07C229/46C07C227/08C07C229/38C07C51/367C07C65/01C07C51/363C07C63/70C07C51/15C07C63/04C07F3/02
CPCC07C227/16C07C227/08C07C51/367C07C51/363C07C51/15C07F3/02C07C2601/14C07C63/04C07C63/70C07C65/01C07C229/38C07C229/46
Inventor 孙学喜杨会来毛杰
Owner 安徽鼎旺医药有限公司
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