Preparation method of trans-4-aminomethylcyclohexanecarboxylic acid

A technology of aminomethylcyclohexyl formic acid and aminomethylcyclohexyl, which is applied in the field of pharmaceutical synthesis, can solve the problems of high price and high production cost, and achieves the effects of simple operation, low cost, broad development and application prospects

Inactive Publication Date: 2015-11-04
SUZHOU JINGYE MEDICINE & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0016] The second method is to use p-carboxybenzylamine as a raw material, through catalytic hydrogenation and conversion, to obtain trans-p-aminomethylcyclohexyl formi

Method used

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  • Preparation method of trans-4-aminomethylcyclohexanecarboxylic acid
  • Preparation method of trans-4-aminomethylcyclohexanecarboxylic acid

Examples

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Embodiment 1

[0035] Embodiment one: the preparation of trans-4-aminomethyl cyclohexyl formic acid (synthetic route such as figure 1 shown).

[0036] (1) Catalytic hydrogenation of 4-hydroxybenzoic acid: Add 100g of 4-hydroxybenzoic acid, 500mL of water, 50g of sodium hydroxide and 10g of Raney nickel into the hydrogenation kettle, and pass in hydrogen to remove the air in the kettle. React at 80°C and a pressure of 5MPa, stop the reaction until no more hydrogen is absorbed, cool the material, filter, adjust the filtrate to pH = 2 with dilute sulfuric acid, filter the precipitated solid, and obtain 4-hydroxycyclohexyl formic acid. Purified directly for the next reaction.

[0037] (2) Esterification of 4-hydroxycyclohexylcarboxylic acid: add 4-hydroxycyclohexylcarboxylic acid, 500mL toluene, 10g p-toluenesulfonic acid and 200g ethanol to the reaction kettle, heat and reflux for 8h under stirring, and cool to 50°C , add 300mL of water, stir and separate the layers, wash the toluene layer o...

Embodiment 2

[0042] Example 2: Preparation of trans-4-aminomethylcyclohexylcarboxylic acid.

[0043] (1) Catalytic hydrogenation of 4-hydroxybenzoic acid: Add 100g of 4-hydroxybenzoic acid, 500mL of water, 60g of sodium hydroxide and 15g of Raney nickel into the hydrogenation kettle, and pass in hydrogen to remove the air in the kettle. React at 90°C and a pressure of 6 MPa, stop the reaction until no more hydrogen is absorbed, cool and discharge, filter, adjust the filtrate to pH = 2 with dilute sulfuric acid, filter the precipitated solid, and obtain 4-hydroxycyclohexyl formic acid. Purified directly for the next reaction.

[0044] (2) Esterification of 4-hydroxycyclohexylcarboxylic acid: Add 4-hydroxycyclohexylcarboxylic acid, 500mL toluene, 10g p-toluenesulfonic acid and 200g ethanol to the reaction kettle, heat and reflux for 10h under stirring, and cool to 50°C , adding 500 mL of water, stirring and separating the layers, washing the toluene layer once with water, and concentrating un...

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Abstract

The invention discloses a preparation method of trans-4-aminomethylcyclohexanecarboxylic acid. Specifically, the method includes the following steps of 1, catalytic hydrogenation of 4-hydroxybenzoic acid; 2, esterification of 4-hydroxyl cyclohexyl formic acid; 3, oxidation of 4-hydroxycyclohexyl formic ether; 4, condensation of 4-oxo cyclohexyl formic ether and nitromethane; 5, catalytic hydrogenation of 4-nitryl methylene cyclohexyl formic ether; 6, hydrolysis and conversion of 4-aminomethyl cyclohexyl formic ether. Compared with the prior art, raw materials used for the preparation method are lower in price and easier to obtain, cost is low, side reactions are fewer, and the yield is higher; meanwhile, the method is easy and convenient to operate and lower in environmental pollution, and has wide development and application prospects.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of trans-4-aminomethylcyclohexylcarboxylic acid. Background technique [0002] The relevant information of trans-p-aminomethylcyclohexylcarboxylate is as follows: [0003] Chinese name: trans-4-aminomethylcyclohexylcarboxylic acid, also known as tranexamic acid or tranexamic acid; [0004] English name: trans -4-aminomethylcyclohexanecarboxylic acid; [0005] CAS: 1197-18-8; [0006] Structural formula: ; [0007] Molecular formula: C 8 h 15 NO 2 ; [0008] Molecular weight: 157.21; [0009] Properties: white crystalline powder; odorless, slightly bitter taste; soluble in water, insoluble in alcohol and chloroform. [0010] The clinical application of tranexamic acid has a long history, and there are many preparation methods. There are mainly two methods for the domestic production of trans-4-aminomethylcyclohexyl formic ac...

Claims

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Application Information

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IPC IPC(8): C07C227/16C07C229/28
CPCC07C51/36C07C67/08C07C67/313C07C201/12C07C227/04C07C227/16C07C62/04C07C69/75C07C205/03C07C229/28
Inventor 沈建伟刘敏
Owner SUZHOU JINGYE MEDICINE & CHEM
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