Preparation process of pebiprofen

A technology for the preparation of pebiprofen and its preparation technology is applied in the field of preparation technology of pebiprofen to achieve the effects of high reaction yield, mild conditions and easy post-treatment

Inactive Publication Date: 2021-07-23
台州市源众药业有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it is very attractive to directly and efficiently construct carbon-carbon double bonds by reacting unactivated cyclohexanone with 2-(4-formylphenyl)propionate, but this direct construction method requires ideal suitable catalyst

Method used

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  • Preparation process of pebiprofen
  • Preparation process of pebiprofen
  • Preparation process of pebiprofen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: a kind of preparation technology of pebiprofen comprises the following steps:

[0031] Step 1: Preparation of methyl 2-(4-bromomethylphenyl)propionate

[0032] Dissolve 2-(4-bromomethylphenyl)propionic acid (32g) in toluene (100ml) solution, add methanol (38g) and concentrated sulfuric acid (17g) successively, and react at 30°C for 5 hours under temperature control, and the reaction is complete , cooling and layering, the organic phase was washed with alkali, washed with water, dried and then concentrated under reduced pressure to obtain 33.4g of the compound 2-(4-bromomethylphenyl)methyl propionate, an orange-yellow transparent oily liquid with a purity of more than 98%.

[0033] Step 2: Preparation of methyl 2-(4-formylphenyl)propionate

[0034] Add 24.5g of hexamethylenetetramine and 50ml of water into the reaction flask, stir to dissolve, add 30g of methyl 2-(4-bromomethylphenyl) propionate and 220ml of ethanol, heat and reflux for 5 hours; add 45ml o...

Embodiment 2

[0040] Embodiment 2: a kind of preparation technology of pebiprofen comprises the following steps:

[0041] Step 1: Preparation of methyl 2-(4-bromomethylphenyl)propionate

[0042]Dissolve 2-(4-bromomethylphenyl)propionic acid (32g) in toluene (100ml) solution, add methanol (38g) and concentrated sulfuric acid (17g) successively, and react at 20°C for 8 hours under temperature control, and the reaction is complete , cooling and layering, the organic phase was washed with alkali, washed with water, dried, and then concentrated under reduced pressure to obtain 30.3 g of the compound 2-(4-bromomethylphenyl) methyl propionate, an orange-yellow transparent oily liquid with a purity of more than 98%.

[0043] Step 2: Preparation of methyl 2-(4-formylphenyl)propionate

[0044] Add 24.5g of hexamethylenetetramine and 50ml of water into the reaction flask, stir to dissolve, add 30g of methyl 2-(4-bromomethylphenyl) propionate and 200ml of ethanol, heat and reflux for 3 hours; add 45ml...

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Abstract

The invention belongs to the field of chemistry, and particularly relates to a novel process for preparing a phenylpropionic acid non-steroidal anti-inflammatory drug pebiprofen. According to the invention, 2-(4-bromomethyl phenyl) propionic acid which is easy to obtain is used as a starting raw material, and the product is prepared by four steps of esterification, hydroformylation, condensation and hydrolysis reaction. The method has the characteristics of simplicity in operation, high reaction selectivity, few byproducts and high product quality.

Description

technical field [0001] The invention belongs to the field of chemical pharmacy, and in particular relates to a preparation process of pebiprofen. Background technique [0002] Pelubiprofen (Pelubiprofen) belongs to phenylpropionic acid non-steroidal anti-inflammatory drugs, its chemical name is: (+)-(E)-2-[4-(2-(oxo-cyclohexylidenemethyl )-phenyl] propionic acid, the structural formula is as follows: [0003] [0004] The synthetic method of pebiprofen has the following several approaches at present: [0005] US Patent No. 4,673,761 discloses the condensation reaction of 1-morpholine cyclohexene and 2-(p-formylphenyl)propionic acid, followed by hydrolysis to obtain the product, and finally recrystallized by ethyl acetate and n-hexane, with a yield of 81%. [0006] [0007] U.S. Patent No. 4,365,076 discloses that cycloheptanone reacts with ethyl 2-(4-formylphenyl)propionate, then hydrolyzes, and obtains pebiprofen by column chromatography. The method uses a strong b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C59/86C07C67/343C07C67/313C07C69/738C07C67/08C07C69/65
CPCC07C51/09C07C67/343C07C67/313C07C67/08C07C2601/14C07C69/65C07C69/738C07C59/86
Inventor 郑人华郭海昌龚华银郑顺罗恒强
Owner 台州市源众药业有限公司
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