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Chemical preparation method of sarafloxacin hydrochloride

A sarafloxacin hydrochloride and chemical technology, applied in the field of chemical preparation of sarafloxacin hydrochloride, can solve the problems of low yield, high cost, and difficult operation, and achieve high purity, low cost, and excellent yield and purity.

Inactive Publication Date: 2011-12-14
XINCHANG HEBAO BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In patent EP0131839 and CN1634890, the piperazine solvent uses DMSO, which is difficult to recover and applies mechanically, as the reaction solvent. It is easy to separate out and difficult to operate during acid-soluble filtration, and the yield is low and the cost is high.

Method used

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  • Chemical preparation method of sarafloxacin hydrochloride
  • Chemical preparation method of sarafloxacin hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] In a 250ml reaction bottle, put 100 g (1.34 mol) n-butanol, 25 g (0.07 mol) 7-chloro-6-fluoro-1-p-fluorophenyl-1,4-oxoquinoline-3-carboxylate acid (hereinafter referred to as carboxylic acid), then add 35g (0.41mol) piperazine, reflux for 10h, recover n-butanol and piperazine, then add 120g (6.67mol) water, add 30% sodium hydroxide alkaline water to adjust the pH value ≥13, dissolve, filter, add 50g (0.85mol) sodium chloride to the filtrate, precipitate insoluble matter, filter, adjust the pH value of the filtrate to 7.0-7.3 with dilute sulfuric acid, and crystallize to obtain the wet product of sarafloxacin, and then add 120g of the wet product In 85% ethanol, heat up and reflux, add reagent hydrochloric acid to adjust the pH value to 2-2.5, cool and crystallize to obtain sarafloxacin hydrochloride (HPLC content ≥ 99%, titration content ≥ 99%, wherein HPLC is high performance liquid chromatography), 18.75 grams, yield 75.0%.

Embodiment 2

[0018] Put 100 g (1.66 mol) of isopropanol and 25 g (0.07 mol) of carboxylic acid into a 250 ml reaction flask, then add 35 g (0.41 mol) of piperazine, keep it under reflux for 10 hours, recover isopropanol and piperazine, and then add 120g (6.67mol) water, add 30% sodium hydroxide alkaline water to adjust the pH value ≥ 13, dissolve, filter, add 75g (1.27mol) sodium chloride to the filtrate, precipitate insoluble matter, filter, adjust the pH value of the filtrate to 7.0- with hydrochloric acid 7.3, crystallization, get the wet product of sarafloxacin, put the wet product into 120g of 85% alcohol again, heat up and reflux, add reagent hydrochloric acid to adjust the pH value to 2-2.5, cool and crystallize to get sarafloxacin hydrochloride (HPLC content≥99% , Titration content≥99%), 18.25 grams, yield 73%.

Embodiment 3

[0020] Put 100 g (1.13 mol) of isoamyl alcohol and 25 g (0.07 mol) of carboxylic acid into a 250 ml reaction flask, then add 35 g (0.41 mol) of piperazine, keep it under reflux for 9 hours, recover isoamyl alcohol and piperazine, and then add 120g (6.67mol) of water, add 30% sodium hydroxide alkaline water to adjust the pH value ≥ 13, dissolve, filter, add 25g (0.34mol) potassium chloride to the filtrate, precipitate insoluble matter, filter, adjust the pH value of the filtrate to 7.0- 7.3, crystallization, get the wet product of sarafloxacin, put the wet product into 120g of 85% alcohol again, heat up and reflux, add reagent hydrochloric acid to adjust the pH value to 2-2.5, cool and crystallize to get sarafloxacin hydrochloride (HPLC content≥99% , Titrated content ≥ 99%), 17.5 grams, yield 70%.

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PUM

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Abstract

The invention mainly discloses a chemical preparation method of sarafloxacin hydrochloride. The method comprises the steps of: performing heat-perservation refluxing on 7-chloro-6-fluoro-1-p-fluoro phenyl-1,4-oxoquinoline-3-carboxylic acid (as shown in formula I in the specification) and piperazine which are used as raw materials in a solvent for 10 hours, and recovering the solvent and the piperazine after reaction; adding water, then adding a sodium hydroxide solution to regulate a pH value to not less than 13, filtering, adding salt into filtrate, filtering, and adding acid in the filtrate to regulate the pH value to 7.0-7.3 to obtain a wet crystal product of sarafloxacin (as shown in a formula II in the specification); and then, adding the wet product of the sarafloxacin (as shown in the formula II in the specification) into 85% ethanol, heating for refluxing, adding hydrochloric acid as a reagent, regulating a pH value to 2-2.5, and cooling and crystallizing to obtain the sarafloxacin hydrochloride (as shown in a formula III in the specification). The chemical preparation method disclosed by the invention has the advantages of easiness for solvent recovery, environment friendliness, high yield 3-5% higher than that of other methods, low cost about 10% lower than that of other methods, high product purity and the like.

Description

technical field [0001] The invention relates to a chemical preparation method of sarafloxacin hydrochloride. Background technique [0002] Sarafloxacin hydrochloride is a quinolone antibiotic, which is widely used as a veterinary drug in the prevention and treatment of bacterial and enzymatic infections in fish, poultry and animals. [0003] Patents CN101108835, EP0131839, and CN1634890 describe the synthesis method of sarafloxacin hydrochloride. CN101108835 uses 7-chloro-6-fluoro-1-p-fluorophenyl-1,4-oxoquinoline-3-carboxylic acid and piper Oxyzine is used as the raw material, after being dissolved in alkali, filtered, crystallized by acid, and hydrogen chloride, which is easy to leak and difficult to transport, is passed into volatile methylene chloride to achieve the purpose of removing impurities, which is a challenge to the environment and safety. [0004] In the patents EP0131839 and CN1634890, the piperazine solvent uses DMSO, which is difficult to recover and applie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/56
Inventor 竺亚庆李思全李品俊陈小刚
Owner XINCHANG HEBAO BIOTECH
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