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Preparation method of Ebastine and fumarate thereof

A technology of fumarate and fumaric acid, which is applied in the preparation of carboxylate, carboxylate, and organic compounds, can solve the problems of high yield and cost, environmental pollution, and high production cost, and achieve environmental protection. Friendly, cost-reducing, and solvent-saving effects

Active Publication Date: 2021-03-30
杭州仟源保灵药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The currently disclosed methods suitable for industrial production to prepare the compound all need to use more solvents. On the one hand, the production cost is high, and on the other hand, it is more likely to cause environmental pollution; In addition, there are problems of higher yield and cost

Method used

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  • Preparation method of Ebastine and fumarate thereof
  • Preparation method of Ebastine and fumarate thereof
  • Preparation method of Ebastine and fumarate thereof

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preparation example Construction

[0030] According to a typical embodiment of the present invention, a 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1- Preparation method of piperidinyl]-1-butanone and fumarate thereof. The preparation method comprises the following steps: 1) mixing 4-(diphenylmethoxy)piperidine, 4'-tert-butyl-4-chlorobutyrophenone, an acid-binding agent and a first solvent to carry out a synthesis reaction, and the reaction ends Then add the second solvent and water, stir and separate to obtain an organic layer and an inorganic layer; Solvent and fumaric acid, filtered and dried to give 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]- 1-butanone or 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone Fumarate; Wherein, the addition volume of the first solvent is 0~2 times of 4-(diphenylmethoxy) piperidine quality, the unit is mL:g, the addition volume of the second solvent is 4-(diphenylmethoxy) 0-5 times the mass of methoxy)piperi...

Embodiment 1

[0038] Add 10.0g of 4-(diphenylmethoxy)piperidine, 11.6g of 4'-tert-butyl-4-chlorobutyrophenone, 7.9g of sodium bicarbonate, and 10ml of toluene into a 250ml three-necked flask, stir and heat up to 110°C , Insulated for 8h and sampled, the conversion rate of raw materials was 96.55%. After cooling down to room temperature, add 40ml of toluene and 60ml of water into the reaction flask, stir for 1h to separate layers, concentrate the organic layer to dryness, add 100ml of ethanol and 4.3g of fumaric acid, filter and dry to obtain 1-[4-(1,1-dimethyl Ethyl) phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone fumarate about 20.0g, yield 91.3% (final product chromatogram Such as figure 1 , where the abscissa is time and the ordinate is absorbance).

Embodiment 2

[0040] Add 10.0g of 4-(diphenylmethoxy)piperidine, 11.6g of 4'-tert-butyl-4-chlorobutyrophenone, and 7.9g of sodium bicarbonate into a 250ml three-necked flask, stir and heat up to 110°C, and keep it warm for 8h Sampling showed that the raw material conversion rate was 93.25%. After cooling down to room temperature, add 50ml of toluene and 60ml of water into the reaction flask, stir for 1h to separate layers, concentrate the organic layer to dryness, add 100ml of ethanol and 4.3g of fumaric acid, filter and dry to obtain 1-[4-(1,1-dimethyl Ethyl) phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone fumarate about 19.5g, yield 89.0% (final product chromatogram Such as figure 2 shown).

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Abstract

The invention discloses a preparation method of Ebastine and fumarate of the Ebastine. The preparation method comprises the following steps: 1) mixing 4-(diphenylmethoxy)-piperidine, 4'-tert-butyl-4-chlorobutyryl benzene, an acid-binding agent and a first solvent to carry out a synthetic reaction, adding a second solvent and water after the reaction is finished, and stirring the reaction productsfor layering to obtain an organic layer and an inorganic layer; and 2) concentrating and drying the organic layer, adding a third solvent or the third solvent and fumaric acid, filtering and drying the mixture to obtain 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(Diphenylmethoxy)-1-piperidinyl]-1-butanone or fumarate thereof. By applying the technical scheme, solvent-free or low-solvent synthesis has the advantages of solvent saving, cost reduction, environmental friendliness and the like.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1 -Piperidinyl]-1-butanone and its fumarate preparation method. Background technique [0002] Ebastine (chemical name: 1-[4-(1,1-dimethylethyl)phenyl]-4-[4-(diphenylmethoxy)-1-piperidinyl]-1-butanone ) 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, chronic idiopathic urticaria, and eczema , asthma, skin itching and other allergic diseases; compared with cetirizine, this product is more effective. [0003] The currently disclosed methods suitable for industrial production to prepare the compound all need to use more solvents. On the one hand, the production cost is high, and on the other hand, it is...

Claims

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Application Information

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IPC IPC(8): C07D211/46C07C51/41C07C57/15
CPCC07D211/46C07C51/412C07C57/15
Inventor 沈杞容王冬冬陶颉丁常英冯乾建潘燕刘锐马小明
Owner 杭州仟源保灵药业有限公司
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