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Green synthesizing process for ofloxacin

A technology of ofloxacin, green synthesis, applied in organic chemistry and other directions, can solve the problems of heavy odor, raw material unit consumption and energy consumption increase, and achieve the effects of good comprehensive effect, good quality and high yield

Active Publication Date: 2009-08-26
ZHEJIANG JINGXIN PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The first, using organic solvents with higher boiling point and higher polarity such as isoamyl alcohol, xylene, dioxane, pyridine, N, N-dimethylformamide or dimethyl sulfoxide as solvent, not only The unit consumption and energy consumption of raw materials are increased, and the smell is heavy, especially dimethyl sulfoxide and pyridine

Method used

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  • Green synthesizing process for ofloxacin
  • Green synthesizing process for ofloxacin
  • Green synthesizing process for ofloxacin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]Weigh 30g of oxyfluorocarboxylic acid (0.1067 moles), 70g of N-methylpiperazine (0.6989 moles), 0.2g of N,N-carbonyldiimidazole (0.0012 moles) and 55g of water (3.0556 moles), and put them into 250ml of reaction Stir in the bottle, heat up to 85°C, and keep the reaction at 85±2°C for 9 hours, and monitor the completion of the reaction by HPLC. After shrinking the piperidine, recover N-methylpiperazine aqueous solution under reduced pressure under the conditions of 90~110°C and -0.09~-0.095MPa until there is basically no flow, then add 180ml tetrahydrofuran to the reaction bottle, heat and reflux for 0.5 hours, and cool down to At about 25°C, keep warm at 25±1°C for 1 hour, filter with suction, rinse the filter cake with tetrahydrofuran until the filtrate is colorless, and then drain it. Put the obtained light yellow solid in a 500ml flask, add 160g of purified water, stir and beat for 30 minutes, then add 30% liquid caustic soda dropwise to the bottle, stir until clear a...

Embodiment 2

[0031] Weigh 30g of oxyfluorocarboxylic acid (0.1067 moles), 60g of N-methylpiperazine (0.5990 moles), 0.15g of cerium trichloride heptahydrate (0.0004 moles) and 40g of water (2.2222 moles), and put into 250ml reaction Stir in the bottle, heat up to 83°C, and keep the reaction at 83±2°C for 7 hours, and monitor the completion of the reaction by HPLC. After shrinking the piperidine, recover the N-methylpiperazine aqueous solution under reduced pressure under the conditions of 90~110°C and -0.09~-0.095MPa until there is basically no flow, then add 220ml of methanol to the reaction bottle, heat and reflux for 0.5 hours, and cool down to At about 25°C, keep warm at 25±1°C for 1 hour, filter with suction, rinse the filter cake with methanol until the filtrate is colorless, and then drain it. Put the obtained light yellow solid in a 500ml flask, add 210g of purified water, stir and beat for 30 minutes, then add 30% liquid caustic soda dropwise to the bottle, stir at 35±1°C until cl...

Embodiment 3

[0033] Weigh respectively 30g of oxyfluorocarboxylic acid (0.1067 moles), 45g of N-methylpiperazine (0.4493 moles), 0.1g of cerium trichloride (0.0004 moles) and 35g of water (1.9444 moles), and drop them into a 250ml reaction flask successively, Stir, heat up to 90°C, and keep the reaction at 90±2°C for 6.5 hours, and monitor the completion of the reaction by HPLC. After shrinking the piperidine, recover the N-methylpiperazine aqueous solution under reduced pressure under the conditions of 90~110°C and -0.09~-0.095MPa until there is basically no flow, then add 250ml of petroleum ether to the reaction bottle, heat and reflux for 0.5 hours, and cool down Heat to about 25°C, keep warm at 25±1°C for 1 hour, filter with suction, rinse the filter cake with petroleum ether until the filtrate is colorless, and then drain it. Put the obtained light yellow solid in a 500ml flask, add 190g of purified water, stir and beat for 30 minutes, then add 30% liquid caustic soda dropwise to the ...

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Abstract

The invention discloses a preparation method for ofloxacin. The prior method uses an organic solvent with higher boiling point and larger polarity, so unit consumption and energy consumption of raw materials are increased and heavy odor is caused; and the prior method adopts other alkaline matters except the reaction raw materials as acid-bonding agents, so solid waste is increased and salt and organic matters in discharged waste water are increased. The preparation method mixes difluorocarboxylic acid, N-methyl piperazine and a catalyst in a reaction solvent for piperazine condensation reaction, obtains a crude product of the ofloxacin after complete reaction and post treatment, and converts the crude product of the ofloxacin into the finished product of the ofloxacin through primary purification treatment; and the reaction solvent is water or a water solution of the N-methyl piperazine. The method takes the water as the reaction solvent and the N-methyl piperazine as the acid-bonding agent, and does not use any other organic solvent and acid-bonding agent to prepare the ofloxacin with good quality and high yield.

Description

technical field [0001] The invention relates to the field of chemical pharmacy, in particular to a preparation method of ofloxacin. Background technique [0002] Ofloxacin (Ofloxacin, OFL) is the third-generation fluoroquinolone antibacterial drug developed by Japan's Daiichi Pharmaceutical Co., Ltd. in 1982, also known as ofloxacin (CAS registration number 82419-36-1), which has an antibacterial spectrum Wide range, strong bactericidal power and high blood drug concentration, bacteria are not easily resistant to drugs, and few side effects, etc., are mainly used clinically for the treatment of various types of infections such as respiratory, urinary, reproductive system, facial features, and skin and soft tissues. This product is white to slightly yellow crystalline powder, odorless, bitter taste, gradually changing color when exposed to light, slightly soluble in water, ethanol, acetone and methanol, easily soluble in glacial acetic acid. Its chemical name is (±)-9-fluoro...

Claims

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Application Information

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IPC IPC(8): C07D498/06
Inventor 张永塘孙海林彭永延钱沛良江霁颜
Owner ZHEJIANG JINGXIN PHARMA
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