Method for preparing efletirizine dihydrochloride

A technology of eflurazine hydrochloride and fluorophenyl, which is applied in the field of preparation of eflurazine hydrochloride, can solve the problems of cumbersome steps and low price of raw material compounds, and achieve the effects of simple raw materials, low cost and simple preparation process

Inactive Publication Date: 2010-12-29
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that it needs distillation and purification under reduced pressure, the price of the raw material compounds of the three reactions is not cheap, and the steps are cumbersome

Method used

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  • Method for preparing efletirizine dihydrochloride
  • Method for preparing efletirizine dihydrochloride
  • Method for preparing efletirizine dihydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Preparation of ethyl 2-[2-[4-[bis(4-fluorophenyl)methyl]-1-piperazinyl]ethoxy]acetate

[0036] 1-[bis(4-fluorophenyl)methyl]piperazine 5.74g (0.02mol), ethyl chloroethoxyacetate 3.34g (0.02mol), triethylamine 4.04g (0.04mol), xylene 30ml , Heated to reflux, added 0.67 g (0.004 mol) of ethyl chloroethoxyacetate after 10 h of reaction and continued to reflux for 8 h. Stop the reaction, filter with suction, wash the filter cake with 20 ml of hot toluene, rotate the filtrate, and directly hydrolyze the residue without purification to obtain eflurizine hydrochloride. Yield 68.5%.

Embodiment 2

[0038] Preparation of Methyl 2-[2-[4-[bis(4-fluorophenyl)methyl]-1-piperazinyl]ethoxy]acetate

[0039] 1-[bis(4-fluorophenyl)methyl]piperazine 5.74g (0.02mol), methyl chloroethoxyacetate 3.05g (0.02mol), triisopropylamine 5.72g (0.04mol), tetrabutyl Ammonium iodide 0.07g (0.2mmol), xylene 30ml, heated to reflux, reacted for 10h, added 0.61g (0.004mol) of ethyl chloroethoxyacetate and continued to reflux for 8h. Stop the reaction, filter with suction, wash the filter cake with 20 ml of hot toluene, rotate the filtrate, and directly hydrolyze the residue without purification to obtain eflurizine hydrochloride. Yield 80.2%.

Embodiment 3

[0041] Preparation of ethyl 2-[2-[4-[bis(4-fluorophenyl)methyl]-1-piperazinyl]ethoxy]acetate

[0042] 1-[bis(4-fluorophenyl)methyl]piperazine 5.74g (0.02mol), ethyl chloroethoxyacetate 3.34g (0.02mol), potassium iodide 0.033g (0.2mmol), triethylamine 4.04g (0.04mol), xylene 30ml, heated to reflux, after 10h of reaction, added 0.67g (0.004mol) of methyl chloroethoxyacetate and continued to reflux for 8h. Stop the reaction, filter with suction, wash the filter cake with 20 ml of hot toluene, rotate the filtrate, and directly hydrolyze the residue without purification to obtain eflurizine hydrochloride. Yield 75.3%.

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Abstract

The invention discloses a method for preparing efletirizine dihydrochloride. 1-bis(4-fluoro phenyl)methyl piperazine and an excessive amount of a chloro(ethoxy)acetic acid derivative are heated to condense in a solvent and in the presence of tertiary amine serving as an acid acceptor and alkali halide or halogenated tetrabutyl ammonium serving as a catalyst to form a [2-[4-[bis(fluorophenyl)methyl]-1-piperazinyl]ethoxy]acetic acid derivative; and the [2-[4-[bis(fluorophenyl)methyl]-1-piperazinyl]ethoxy]acetic acid derivative is hydrolyzed and acidized to form the efletirizine dihydrochloride. The method has the advantages of readily available raw materials, simple and convenient operation, high yield and low cost and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing eflurazine hydrochloride, and the compound can treat allergic rhinitis and conjunctivitis. Background technique [0002] Allergic rhinitis (Allergic Rhinitis), also known as allergic rhinitis, is caused by the body's allergy to certain substances. Its pathogenesis is that allergens cause the body to release histamine, causing a series of allergic symptoms to appear. The clinical features of this disease include nasal itching, continuous sneezing, and a large amount of watery nasal discharge, sometimes accompanied by extreme itching in the conjunctiva, palate, and even the external auditory canal. Due to the swelling of the nasal mucosa, patients often have nasal congestion and hyposmia. Patients usually have no obvious systemic symptoms, but if complicated by sinusitis, they may have symptoms such as fever, cheek distending pain, fatigue and anorexia. [0003] The treatment principles of this disease a...

Claims

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Application Information

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IPC IPC(8): C07D295/088
Inventor 马丽芳陈姜涛杜翔宇
Owner SICHUAN UNIV
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