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Method for preparing ebastine

A technology of ebastine and benzophenone, which is applied in the field of preparation of ebastine, can solve the problems of high cost, high cost of ebastine, high production cost, etc., and achieve simple operation, high yield, low cost effect

Active Publication Date: 2019-04-09
JIANGSU LIANHUAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, these two methods have caused the high production cost of these two methods due to the use of higher cost raw materials diphenylbromomethane and diphenylmethanol, which has caused the cost of ebastine to increase.

Method used

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preparation example Construction

[0029] A kind of preparation method of ebastine, take benzophenone as starting raw material, condense with 4-hydroxypiperidine to obtain 4-dibenzyloxypiperidine, then with 4-chloro-1-(4-tert Butylphenyl)-1-butanone is condensed to obtain Ebastine.

[0030] Ebastine (Ebastine) alias Kaisiting; Ebadine; Secodine; Ebastel; Kestine, the chemical name is 1-(4-tert-butylphenyl)-4-[4-(diphenylmethoxy Base)-1-piperidinyl]-1-butanone, a non-hygroscopic, white crystalline powder. Molecular formula: C 32 h 39 NO 2 , molecular weight: 469.65800, melting point: 80-82°C. Its antihistamine activity is competitive at low concentrations and non-competitive at high concentrations. It is clinically used for allergic diseases, including allergic rhinitis in children, perennial rhinitis in adults, seasonal rhinitis, hay fever and chronic urticaria.

[0031] The preparation method of ebastine provided by the present invention has changed the high-cost method of preparing ebastine from relativ...

Embodiment 1

[0053] The preparation method of the ebastine provided by the present embodiment specifically comprises the following steps:

[0054] (1) Add benzophenone (30g, 0.165mol) into 300mL toluene solution, stir to dissolve, then add aluminum trichloride (2.2g, 0.017mol), trifluoromethanesulfonic acid (2.5g, 0.018mol) ), heated up to 50°C and stirred for 20min, cooled to room temperature, added p-toluenesulfonic acid (31.2g, 0.18mol), added 4-hydroxypiperidine (17.2g, 0.17mol), heated to reflux state, kept warm and refluxed with water to react 5h, after the reaction, the reaction solution was cooled to room temperature, slowly added 1N NaOH solution 230mL under ice bath cooling, stirred and neutralized for 30min, left to stand for 30min to separate liquid, separated to remove the water layer, and then added sodium bicarbonate (35g, 0.41 mol), 4-chloro-1-(4-tert-butylphenyl)-1-butanone (37.5g, 0.157mol), warming up to reflux state, keeping warm at reflux with water for 12h, cooling to...

Embodiment 2

[0057] The preparation method of the ebastine provided by the present embodiment specifically comprises the following steps:

[0058] (1) Add benzophenone (50g, 0.275mol) in 500mL methyl isobutyl ketone solution, stir to dissolve, add aluminum trichloride (3.7g, 0.028mol), trifluoromethanesulfonic acid (4.2 g, 0.03mol), heated to 50°C and stirred for 20min, cooled to room temperature, added p-toluenesulfonic acid (52.1g, 0.31mol), added 4-hydroxypiperidine (28.7g, 0.28mol), heated to reflux state, and kept Reflux and react with water for 5 hours. After the reaction, cool the reaction solution to room temperature, slowly add 385mL of 1N NaOH solution under ice bath cooling, stir for 30 minutes, let stand for 30 minutes to separate the liquid, separate the water layer, add sodium bicarbonate to the organic layer (58.5g, 0.68mol), 4-chloro-1-(4-tert-butylphenyl)-1-butanone (62.6g, 0.262mol), heated to reflux state, kept warm and refluxed with water for 12h, and the reaction ended...

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Abstract

The invention provides a method for preparing ebastine. The method comprises the following steps: condensing an initial raw material benzophenone and 4-hydroxypiperidine to obtain 4-benzhydryloxypiperidine; condensing with 4-chloro-1-(4-tert-butylphenyl)-1-butanone to obtain ebastine. According to the method, benzophenone with low price is used as the initial raw material, has low cost and is simple and convenient to operate, only one reaction kettle is used, alkaline washing and rinsing are performed in the middle process, and the final product can be obtained by freezing and crystallizing with alcohol. The method has the advantages of good economic benefit, high safety, high yield, good purity and the like, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical engineering, in particular to a preparation method of ebastine. Background technique [0002] Ebastine is a long-acting, non-sedating second-generation histamine H1 receptor antagonist, which has a significant curative effect in the treatment of allergic rhinitis, has a small drowsiness effect, and is convenient to take; it is used for seasonal, allergic rhinitis and chronic idiopathic urticaria. The treatment of allergic diseases such as measles, eczema, asthma, skin pruritus; compared with cetirizine, this product is more effective. In addition, recent foreign studies have also shown that it has the effect of anti-angiogenesis, and it is expected to be applied to the treatment of asthma and bronchitis. [0003] Currently disclosed methods suitable for industrial production and preparation of ebastine mainly contain two kinds: 1, 4-chloro-1-(4-tert-butylphenyl)-1-butanone and 4-hyd...

Claims

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Application Information

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IPC IPC(8): C07D211/46
CPCC07D211/46
Inventor 吴为贲
Owner JIANGSU LIANHUAN PHARMA
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