Environment-friendly method for preparing levofloxacin hydrochloride

A levofloxacin hydrochloride, green and environmentally friendly technology, applied in the field of organic compound synthesis, can solve the problems of increased post-processing workload and three wastes, poor environmental protection and economic efficiency, increased recycling energy consumption, etc., to reduce environmental pollution and industrial raw material consumption, production costs Low, the effect of increasing the yield

Inactive Publication Date: 2017-09-01
TAICANG CUSTOM NEW MATERIALS CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis process reported in the literature also has many defects, which are as follows: (1) the first step does not separate triethylamine hydrochloride, and directly enters the second step, and the waste water produced will contain triethylamine hydrochloride and diethylamine hydrochloride at the same time. Methylamine acetate; (2) In the second step, toluene is dried with a desiccant, which will produce solid waste; (3) In the third step, potassium carbonate and toluene system are used. Because the solubility of potassium carbonate inorganic salts in toluene is too poor, the reaction It is not ideal, the yield is un

Method used

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  • Environment-friendly method for preparing levofloxacin hydrochloride

Examples

Experimental program
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Example Embodiment

[0043] Example 1

[0044] Such as figure 1 The synthetic method of levofloxacin hydrochloride shown includes the following steps:

[0045] (1) Preparation of 3-(2-hydroxy-1-methyl-ethylamino)-2-(2,3,4,5-tetrafluorobenzoyl)-ethyl acrylate

[0046] Add 29.2g of N,N dimethylamino ethyl acrylate, 22.7g of triethylamine and 340ml of toluene into a three-necked flask, heat to 50°C with stirring, and slowly add 42.5g of tetrafluorobenzoyl chloride / toluene solution dropwise. Add 1.5 hours, keep it for 3 hours after dripping, the conversion is 97%, cool, filter about 24.2g of triethylamine hydrochloride, a small amount of toluene to wash the triethylamine hydrochloride filter cake, the filtrate is heated to 50 ℃, drip 15g L-2-Aminopropanol, drip in half an hour, heat to 90°C, keep it warm for 1 hour, convert 98%, cool, wash twice, layer the toluene phase, spin dry and dehydrate, add DMF to dilute to 250ml, liquid The phase purity is 99.16%.

[0047] (2) Preparation of levox main cyclic acid...

Example Embodiment

[0052] Example 2

[0053] Such as figure 1 The synthetic method of levofloxacin hydrochloride shown includes the following steps:

[0054] (1) Preparation of 3-(2-hydroxy-1-methyl-ethylamino)-2-(2,3,4,5-tetrafluorobenzoyl)-ethyl acrylate

[0055] Add 29.2g of N,N dimethylamino ethyl acrylate, 20.2g of triethylamine and 340ml of toluene into a three-necked flask, heat to 40℃ with stirring, slowly add 45g of tetrafluorobenzoyl chloride / toluene solution, dropwise 1 hour, keep for 2 hours after dripping, conversion 96%, cooling, filter about 24.8g triethylamine hydrochloride, a small amount of toluene wash the triethylamine hydrochloride filter cake, the filtrate is heated to 40 ℃, drop 16g of L -2-Aminopropanol, drip in half an hour, heat up to 90℃, keep for 0.5 hour, convert 98%, cool, wash three times, layer toluene, spin dry and dehydrate, add DMF to dilute to 250ml, liquid purity 99.22%.

[0056] (2) Preparation of levox main cyclic acid

[0057] Add potassium carbonate and DMF int...

Example Embodiment

[0061] Example 3

[0062] Such as figure 1 The synthetic method of levofloxacin hydrochloride shown includes the following steps:

[0063] (1) Preparation of 3-(2-hydroxy-1-methyl-ethylamino)-2-(2,3,4,5-tetrafluorobenzoyl)-ethyl acrylate

[0064] Add 29.2g of N,N dimethylamino ethyl acrylate, 24.3g of triethylamine and 340ml of toluene into a three-necked flask, heat to 60°C with stirring, and slowly add 51g of tetrafluorobenzoyl chloride / toluene solution dropwise. 2 hours, keep for 4 hours after dripping, convert 97%, cool, filter about 25.2g of triethylamine hydrochloride, wash the filter cake of triethylamine hydrochloride with a small amount of toluene, warm the filtrate to 60℃, add 18g of L dropwise -2-Aminopropanol, drip in half an hour, heat to 90℃, keep for 1.5 hours, convert 98%, cool, wash twice, toluene phase layering, spin dry and dehydration, add DMF to dilute to 250ml, liquid phase The purity is 99.41%.

[0065] (2) Preparation of levox main cyclic acid

[0066] Add po...

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Abstract

The invention provides an environment-friendly method for preparing levofloxacin hydrochloride. The method comprises the following steps: preparing 3-(2-hydroxy-1-methyl-ethylamino)-2-(2,3,4,5-tetrafluorobenzoyl)-ethyl acrylate, preparing levo-oxy main naphthenic acid, and preparing the levofloxacin hydrochloride. The method provided by the invention is concise, low in production cost, high in product yield, good in quality, economic and environment-friendly, fewer three wastes are discharged, and most byproducts are effectively separated and recycled, so that the method is convenient for industrial production and has great popularization significance.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to an environmentally friendly method for preparing levofloxacin hydrochloride. Background technique [0002] Fluoroquinolones have achieved great success in clinical anti-infective treatment due to their high efficiency, broad antibacterial spectrum and low toxicity. The chemical name of levofloxacin hydrochloride is (s)-(-)-9-fluoro-2,3-dihydro-3-methyl-10-[4-methyl-1-piperazinyl]-7-oxo- 7-hydropyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate hydrochloride. [0003] At present, the domestic industrialized production of levofloxacin is mainly based on (2,3,4,5)-tetrafluorobenzoic acid as raw material, after acid chlorination, coupling with N,N-dimethylaminoethyl acrylate, and replacement with L-aminopropanol. , Cyclization, hydrolysis and condensation with N-methylpiperazine refined. In 2005, "Journal of Chemical Engineering of Universities" No. 5, V...

Claims

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Application Information

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IPC IPC(8): C07D498/06
CPCC07D498/06
Inventor 李瑞清
Owner TAICANG CUSTOM NEW MATERIALS CO LTD
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