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Synthesis method of 2-methyl piperazine lomefloxacin

A technology of methylpiperazine and synthesis method, applied in the field of synthesis of 2-methylpiperazine lomefloxacin, to achieve the effects of eliminating the use of reagents, reducing hazards, and shortening reaction time

Inactive Publication Date: 2012-02-15
ZHANGJIAKOU GERUI HIGH TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] But, there is no report of synthesizing this compound so far, Chinese patent CN101659654A (disclosure date is March 3, 2010) discloses a kind of preparation method of compound I

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The first step. The preparation of formula IX compound i.e. 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid diacetate boron chelate compound:

[0031] Add 1.94 g of boric acid and 4 ml of acetic acid into a 100 ml four-neck flask equipped with a mechanical stirrer, a spherical condenser, a thermometer and a dropper, and heat the reaction solution to 90° C. while stirring. Add 11.5ml of acetic anhydride dropwise at a rate of 6-15ml / min, react at 110°C for 30 minutes, cool down to below 80°C, add 1-ethyl-6,7,8-trifluoro-1,4-dihydro -4-oxoquinoline-3-carboxylic acid (compound Ⅷ) 6.78g (0.025mol), heat to reflux for about 8 hours, TLC detects that there is no compound Ⅷ in the reaction solution, then cool down to room temperature, cool in an ice-water bath and add under rapid stirring 50ml of ice water gradually became turbid and solids were precipitated. Suction filter, wash with water until neutral (pH5-6), dry under vacuum below 40°C until constant ...

Embodiment 2

[0037] The first step. The preparation of formula IX compound i.e. 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid diacetate boron chelate compound:

[0038] Add 19.4 g of boric acid and 40 ml of acetic acid into a 1000 ml four-neck flask equipped with a mechanical stirrer, a spherical condenser, a thermometer and a dropper, and heat the reaction solution to 90° C. while stirring. Add 120ml of acetic anhydride dropwise at a rate of 6-15ml / min, react at 110°C for 30 minutes, cool down to below 60°C, add 1-ethyl-6,7,8-trifluoro-1,4-dihydro- 4-oxoquinoline-3-carboxylic acid (compound Ⅷ) 67.8g (0.25mol), heated to reflux for about 8 hours, TLC detected that there was no compound of formula Ⅷ in the reaction liquid, then cooled to room temperature, cooled in an ice-water bath and added under rapid stirring 600ml of ice water gradually became turbid and solids were precipitated. Suction filter, wash with water until neutral (pH5-6), dry under vacuum below 40°C ...

Embodiment 3

[0044] The first step. The preparation of formula IX compound i.e. 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid diacetate boron chelate compound:

[0045] Add 77.5 g of boric acid and 160 ml of acetic acid into a 3000 ml four-necked flask equipped with a mechanical stirrer, a spherical condenser, a thermometer and a dropper, and heat the reaction solution to 90° C. while stirring. Add 475ml of acetic anhydride dropwise at a rate of 6-15ml / min, react at 110°C for 30 minutes, cool down to below 90°C, add 1-ethyl-6,7,8-trifluoro-1,4-dihydro- 4-oxoquinoline-3-carboxylic acid (compound Ⅷ) 217g (0.80mol), heat to reflux for about 8 hours, TLC detects that there is no compound Ⅷ in the reaction solution, then cool down to room temperature, cool in an ice-water bath and add ice water under rapid stirring 1000ml, gradually became turbid and precipitated solid. Suction filter, wash with water until neutral (pH5-6), dry under vacuum below 40°C until constant weig...

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Abstract

The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of 2-methyl piperazine lomefloxacin. A report for synthesizing the compound is not yet heard, and Chinese patent CN101659654A discloses a preparation method of the compound. At present, the 2-methyl piperazine lomefloxacin is prepared by simulating the preparation method. The preparation methodcan be completed by four steps, wherein two-step reaction is needed in removal of a chelate compound and a tert-butoxy carbonyl, and each step is completed for long time. The synthesis method comprises the following three steps of: preparing 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid into a 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic oxalic acid boronchelate compound, preparing a 1-ethyl-6,8-difluoro-7-(2-methyl-4-tert-butoxy carbonyl-1-piperazine)-1,4-dihydro-4-oxoquinoline-3-carboxylic oxalic acid boron chelate compound, and preparing a 1-ethyl-6,8-difluoro-7-(2-methyl-1-piperazine)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (a compound of the formula XI, the 2-methyl piperazine lomefloxacin).

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of 2-methylpiperazine lomefloxacin. Background technique [0002] The chemical name of 2-methylpiperazine lomefloxacin is 1-ethyl-6,8-difluoro-7-(2-methyl-1-piperazinyl)-1,4-dihydro-4-oxo Quinoline-3-carboxylic acid (hereinafter referred to as 2-methylpiperazine lomefloxacin) is one of the main impurities of fluoroquinolone lomefloxacin hydrochloride. The smaller the content of lomefloxacin hydrochloride, the better, but absolutely no is difficult to do. In order to objectively evaluate the content of 2-methylpiperazine lomefloxacin in the lomefloxacin hydrochloride crude drug, there must be a 2-methylpiperazine lomefloxacin reference substance, which is used for the control test with lomefloxacin hydrochloride to detect lomefloxacin hydrochloride The amount of 2-methylpiperazine lomefloxacin in methfloxacin can be used to determine whether the qua...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
Inventor 李君孙文王毅卢鹏
Owner ZHANGJIAKOU GERUI HIGH TECH
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