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Environmentally-friendly preparation method of ciprofibrate

An environment-friendly, dichlorocyclopropyl-based technology, applied in the field of environment-friendly preparation of ciprofibrate, can solve problems such as unsuitability for large-scale industrial production, potential safety hazards or pollution, and achieve mild conditions and high safety Sexuality and easy-to-control effects

Inactive Publication Date: 2014-04-09
安徽安腾药业有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The existing technology uses a large amount of peroxyacid or hydrogen peroxide, which has potential safety hazards or pollution, and is not suitable for large-scale industrial production

Method used

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  • Environmentally-friendly preparation method of ciprofibrate
  • Environmentally-friendly preparation method of ciprofibrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] 1) Preparation of p-hydroxystyrene from p-hydroxybenzaldehyde

[0067] Add 833g of p-hydroxybenzaldehyde and 2500ml of pyridine into a 10L flask, weigh 1450g of malonic acid, add to the reaction flask in batches and stir, add dropwise 140ml of piperidine, finish adding in 30min, and then reflux until the reaction is complete. The solvent was spin-dried, and 4000ml of water and 3000ml of dichloromethane were added, and the aqueous layer was washed with 2000ml of dichloromethane, and the organic phases were combined, washed with 7000ml of 10% citric acid aqueous solution, dried with anhydrous sodium sulfate, and distilled under reduced pressure to obtain 675g of the product. The molar yield is 83%.

[0068] 2) Preparation of 1-benzyloxy-4-styrene from p-hydroxystyrene

[0069] Dissolve 277g p-hydroxystyrene in 1000ml acetone, add 586g K 2 CO 3 , Add 351g of benzyl chloride dropwise, then heat the reaction to 57°C, reflux until the reaction is complete, and filter. ...

Embodiment 2

[0077] 1) Preparation of p-hydroxystyrene from p-hydroxybenzaldehyde

[0078] Add 400g of p-hydroxybenzaldehyde and 1000ml of pyridine to a 10L flask, weigh 681g of malonic acid, add to the reaction flask in batches, stir, and heat to reflux until the reaction is complete. Recover the solvent under reduced pressure, add 2000ml of water and 2000ml of dichloromethane, wash the aqueous layer with 2000ml of dichloromethane, combine the organic phases, then wash with 2000ml of 10% aqueous hydrochloric acid, dry with anhydrous sodium sulfate, and distill under reduced pressure to obtain 330g of the product. The molar yield is 84.1%.

[0079] 2) Preparation of 4-(methoxymethoxy)styrene from p-hydroxystyrene

[0080] Dissolve 200g of p-hydroxystyrene in 500ml of tetrahydrofuran, lower the temperature to 0°C, add 73.3g of 60% NaOH in batches, and after stirring for half an hour, add 141g of chloromethyl methyl ether dropwise, raise the temperature to 20-25°C, and stir until The ...

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Abstract

The invention provides a brand new preparation method of ciprofibrate. The method is characterized in that the method comprises the following steps: decarboxylating cheap and easily-available p-hydroxybenzaldehyde as a raw material, carrying out hydroxy group protection, cyclizing, deprotecting, and carrying out a Bargellini reaction to prepare ciprofibrate. Compared with traditional methods, the method provided by the invention has the advantages of simple operation, mild and easily-controlled conditions, post-treatment convenience, environmental protection and high yield, has a high safety because of the avoiding of the use of a large amount of peroxy acid or hydrogen peroxide, and is a brand new environmentally-friendly method suitable for the industrial synthesis of ciprofibrate.

Description

technical field [0001] The invention relates to the technical field of preparation of blood lipid-lowering drugs, in particular to a brand-new environment-friendly preparation method for preparing ciprofibrate by using p-hydroxybenzaldehyde as a raw material. Background technique [0002] Ciprofibrate, also known as clofibrate, is a phenoxyacetic acid hypolipidemic drug, which is stronger than clofibrate. Can significantly reduce very low density and low density lipoprotein levels, and increase high density lipoprotein. It also dissolves fibrin and prevents platelet aggregation. The chemical name is 2-[4-(2,2-dichlorocyclopropyl)phenoxy]-2-methylpropionic acid, and its structural formula is: [0003] [0004] Its synthetic method mainly contains following several kinds at present: In CN1514819A, disclose a kind of with compound 2,2-dichlorocyclopropyl benzene as raw material, through Friedel-Crafts acylation, carry out Baeyer-Villiger gravity with the effect of peroxyac...

Claims

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Application Information

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IPC IPC(8): C07C59/72C07C51/02
CPCC07C37/002C07C37/055C07C39/42C07C41/09C07C41/30C07C51/16C07C2601/02C07C59/72C07C43/225C07C43/215C07C39/20Y02P20/55
Inventor 李新涓子汪迅李勇刚张兆国高艳吕兴红沈小良王卓夏小波
Owner 安徽安腾药业有限责任公司
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