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A technology of amino and dimethylamino, which is applied in the field of pharmaceutical preparation, achieves good recovery rate, reduces production cost, and is beneficial to centralized treatment and recovery.
Active Publication Date: 2011-12-14
YUEYANG YETOP FINE CHEM
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The disadvantage of this method is that the direct reduction of acid to alcohol requires the use of a strong reducing agent such as lithium aluminum hydride, the preparation process is very easy to catch fire, the risk is high, and there are also disadvantages such as high price of auxiliary raw materials, high cost, and large pollution.
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Embodiment 1
[0032] In a 2L four-necked bottle, add 150g of 30% sodium hydroxide aqueous solution, add 180g of 2-amino-2-phenylbutyric acid under stirring, stir for 1 hour, add 30% sodium hydroxide aqueous solution in an appropriate amount, control the pH=10, reduce Distilled water until viscous, cooled, filtered, and dried to obtain 200 g of 2-amino-2-phenylbutyric acid sodium salt.
[0033] Add 200g of 2-amino-2-phenylbutyric acid sodium salt and 500ml of xylene to a 2L four-neck flask, heat to 110°C, add 300g of dimethyl sulfate dropwise, keep stirring for 2 hours after the dropwise addition, and cool to 60± 2°C, add water, stir and cool to room temperature. Separate the layers, remove the water layer, recover the solvent under reduced pressure, and then rectify under high vacuum (2~3mmHg) to obtain the product to obtain 195g of methyl 2-(dimethylamino)-2-phenylbutyrate, with a yield of 88%.
[0034] In a 500ml four-necked bottle, slowly add 25g of anhydrous zinc chloride to 100ml of ...
Embodiment 2
[0037] In a 2L four-necked bottle, add 150g of 30% sodium hydroxide aqueous solution, add 180g of 2-amino-2-phenylbutyric acid under stirring, stir for 1 hour, add 30% sodium hydroxide aqueous solution in an appropriate amount, control the pH=10, reduce Distilled water until viscous, cooled, filtered, and dried to obtain 200 g of 2-amino-2-phenylbutyric acid sodium salt.
[0038] Add 200g 2-amino-2-phenylbutyric acid sodium salt and 600ml toluene to a 2L four-necked flask, heat to reflux, add 300g dimethyl sulfate dropwise, keep stirring for 2 hours after the dropwise addition, and cool to 60±2°C , add water, stir and cool to room temperature. Separate the layers, remove the water layer, recover the solvent under reduced pressure, and then rectify the product under high vacuum (2~3mmHg) to obtain 199g of methyl 2-(dimethylamino)-2-phenylbutyrate, with a yield of 90%.
[0039] In a 500ml four-necked bottle, slowly add 25g of anhydrous aluminum trichloride to 100ml of ethylene ...
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Abstract
The invention relates to medicine preparation methods, particularly a preparation method of trimebutine, which comprises the following steps: esterifying and amino-methylating 2-amino-2-phenylbutyric acid which is used as the raw material, and reducing into 2-(dimethylamino)-2-phenylbutyl alcohol; and synthesizing trimebutine from the 2-(dimethylamino)-2-phenylbutyl alcohol and 3,4,5-trimethoxybenzoic acid in an organic solvent by using protonic acid as a catalyst. The invention is characterized in that the esterification and amino-methylation of the 2-amino-2-phenylbutyric acid are carried out at the same time to obtain the 2-(dimethylamino)-2-phenylmethyl butyrate, and sodium borohydride is used for reduction to obtain the 2-(dimethylamino)-2-phenylbutyl alcohol. In the invention, the 2-amino-2-phenylbutyric acid is subjected to esterification and amino-methylation at the same time, and reduced into alcohol, thereby simplifying the operation, greatly reducing the production risk, enhancing the reaction yield (up to higher than 80%) and greatly lowering the raw material cost. In the last preparation step, the protonic acid is added, thereby reducing the feed amount of the 3,4,5-trimethoxybenzoic acid and lowering the reaction cost.
Description
technical field [0001] The invention relates to a preparation method of medicine, in particular to a preparation method of trimebutine. Background technique: [0002] Trimebutine is used to treat chronic gastritis and irritable bowel syndrome. As a drug for regulating gastrointestinal motility, the incidence of adverse reactions is only about 4.3%, and it disappears naturally after continuing to take it. There are no cases of forced drug withdrawal. It has achieved relatively great success in clinical treatment, and it is one of the main gastrointestinal drugs on the market. [0003] [0004] (I) [0005] Trimebutine [0006] The synthesis research of trimebutine has been continuously improved and improved in the past ten years, and the current main production methods are mainly: [0007] 1. Prepare trimebutine with propiophenone as raw material, such as patent PCT2001021601, synthesize 2-methyl-4-ethyl-4-phenyl-2-oxazoline with propiophenone as raw material, and t...
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