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Preparation method of fexofenadine

A fexofenadine and solvent technology, applied in the field of chemical synthesis, can solve the problems of large environmental impact, difficult to control, difficult to recycle, etc., and achieves the effects of low cost, few reaction steps, and easy operation

Pending Publication Date: 2021-04-16
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since this method uses HgO, which is harmful to the human body and difficult to recycle and treat, it has a greater impact on the environment in the production project.

Method used

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  • Preparation method of fexofenadine
  • Preparation method of fexofenadine
  • Preparation method of fexofenadine

Examples

Experimental program
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Effect test

preparation example Construction

[0052]The synthesis method contains the following steps:

[0053]Step 1: Tielobutyrate is a raw material, react with trimethylchlorosilane under basic conditions under alkaline conditions to form 1-methoxy-1- (trimethylsiloxysiloxy) -2-methyl-1-propylene (I);

[0054]Step 2: Four-gramyl chloride reaction to 4-chlorocyanl chloride is carried out in a p-bromobenzene, forming 4'-bromo-4-chlorobenzine (II);

[0055]Step 3: 4'-bromo-4-chlorobenzone (II) with 1-methoxy-1- (trimethylsiloxy) -2-methyl-1-propylene (I) coupling The reaction was obtained from 2- [4- (4-chloro-1-butyl) phenyl] -2-methylpropylene (III);

[0056]Step 4: 2- [4- (4-chloro-1-butyl) phenyl] -2-methylpropylene methyl ester (III) reacts 2- [4- [4- [4 " - (Hydroxybenzyl)-1-piperidyl] -1-oxineyl] phenyl] -2,2-dimethyl acetate (IV);

[0057]Step 5: 2- [4- [4- [4- (Hydroxybenzyl)-1-piperidyl] -1-oxineyl] phenyl] -2,2-dimethyl acetate (Iv) reduction is 2- [4- [4- [4- (hydroxybenzyl)-1-piperidyl] -1-hydroxybutyl] phenyl] -2,2-dimethyl acet...

Embodiment 1

[0067]Example 1: In a nitrogen atmosphere, the methyl ester 500 g, 5L tetrahydrofuran is added to -20 ° C, slowly dropped with diisopropylamamine (3L, 2M IN THF), and dripping, shift To the room temperature reaction for 2 h, then removed to -20 ° C, add 600 g of trimethylchlorosilane, end, and moved to room temperature, there is a large amount of solid production, add n-hexane dilution, add aqueous solution, and separate liquid, collect organic phase After washing with saturated brine, the saline, dried over anhydrous sodium sulfate was dried, and the yield was obtained from a pale yellow oily liquid compound (I), and the yield was 98%.

Embodiment 2

[0068]Example 2: In a nitrogen atmosphere, methyl isobutyrate 500 g, 5L tetrahydrofuran, cooled to -20 ° C, slowly dropped the double trimethylsil-based lithium (3L, 2M in THF), and end the drop , Moved to a room temperature reaction for 2 h, then moved to -20 ° C, add 600 g of trimethylchlorosilane, end, moved to room temperature, there is a large amount of solid production, add n-hexane dilution, then add aqueous solution, and collect, collect, collect The organic phase, then washed 3 organic phases, dried over anhydrous sodium sulfate, and yields were obtained by mixed brine, and yield was 97%.

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Abstract

The invention provides a preparation method of fexofenadine, which comprises the following steps: by using bromobenzene as a raw material, carrying out Friedel-Crafts acylation reaction to obtain 4'-bromo-4-chlorophenone ; enabling 4'-bromo-4-chlorobutanone and 1-methoxy-1-(trimethylsiloxy)-2-methyl-1-propene to subjected to coupling reaction to obtain 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methyl methyl propionate; and sequentially carrying out N-alkylation, carbonyl reduction and alkaline hydrolysis on 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methylpropanoate to obtain fexofenadine. The method has the advantages of cheap and easily available raw materials, easiness in operation, high yield, low cost, no meta-isomer, suitability for industrial production and the like.

Description

Technical field[0001]The present invention relates to a synthetic method of antimonymine drugs, and is a chemical synthesis technique, and in particular, it relates to highly efficient synthesis of non-So-Noneta, as a coupling reaction as a key step, specifically a non-So Non-Non-Non. method.Background technique[0002]Non-Nonote is known 2- [4- [1-hydroxy-4- [4- (hydroxy diphenyl)-1-piperidyl] butyl] phenyl] -2-methylpropylene Acid, molecular formula C32Hide39NO4It is used in clinically, has a hydrochloride salt thereof. Nonodia is a new generation of receptor antagonics, which is a receptor antagonist, which is German Hermelo (HMR), developed and developed in 1996, was listed in the United States after approval by FDA. Allegra, followed by countries such as Britain, Sweden, Australia, and sales in China are also increasing. As a safe alternative, it has good economic and social benefits.[0003]There are more literature and patents of Non Nodia, mainly:[0004]1. Process 1 (US 4254129),...

Claims

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Application Information

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IPC IPC(8): C07D211/22
CPCY02P20/55
Inventor 高锦明王震郑杰赵鹏
Owner NORTHWEST A & F UNIV
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