ChemicalBook CAS DataBase List Tranexamic Acid

Tranexamic Acid synthesis

11synthesis methods

Product Name:Tranexamic Acid
CAS Number:1197-18-8
Molecular formula:C8H15NO2
Molecular Weight:157.21

Tranexamic acid, trans-4-(aminomethyl)cyclohexane carboxylic acid (24.4.5), is synthesized from 4-methylbenzonitrile. Oxidation of the methyl group gives the mononitrile of terephthalic acid 24.4.2. The cyano group in this compound is reduced by hydrogen using Raney nickel as a catalyst. The benzene ring of the resulting 4- aminomethylbenzoic acid (24.4.3) is reduced to a cyclohexane moiety by hydrogen and a platinum catalyst, which forms an isomeric mixture of 4-aminomethylcyclohexane carboxylic acids (24.4.4), and the desired trans-isomer 24.4.5 is isolated by crystallization of the mixture of its sodium salts.

4-(Acetylamino-methyl)-cyclohexanecarboxylic acid methyl ester

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Yield:1197-18-8 85.11%

Reaction Conditions:

with barium hydroxide octahydrate;hydrogen in ethanol;water at 250; under 7500.75 - 30003 Torr; for 7.5 h;Pressure;Temperature;

Steps:

5 Preparation of trans-4-aminomethylcyclohexylformic acid

To a 1 L hydrogenation kettle, methyl 4-acetamidomethylcyclohexylcarboxylate (28. 00 g, 0.13 mol), 100 mL of ethanol, 200 mL of water,Barium hydroxide octahydrate (95. 82g, 0.30mol), shut down the reaction dad, pass the IMPa hydrogen to replace the air 3 times (or replace with nitrogen)And then pass 1MPa of hydrogen leak detection, if not leak, the pressure transferred to 4MPa, stir to raise the temperature to 250 ° C reaction 7. 5 hours,Stop the reaction, open the kettle, the reaction solution poured out, placed in a reaction flask, add water 200mL, heated to 70 ° C,Neutralized with carbon dioxide to pH 3. 3, barium carbonate was removed by filtration, the filtrate was adjusted to pH 3 with sulfuric acid, allowed to stand for 3 hours, filtered, washed with water,Add 5 g of activated charcoal decolorization, filtration, the filtrate sprinkled to 50mL, then add ethanol 50mL crystallization, cooling to 10 ° C, filtration, crystallization with ethanol washing, drying, white solid trans-4-aminomethylcyclohexylformic acid, Mass of 17.37g, mp: 384-388 ° (decomposition), molar yield of 85.11% By liquid phase detection, trans-body content of 99.6910%

References:

CN104151183,2016,B Location in patent:Paragraph 0051-0053