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Novel synthetic method of aripiprazole and intermediate thereof

A kind of technology of aripiprazole and synthesis method, applied in the field of synthesis of antipsychotic drug - aripiprazole, to achieve the effects of fast reaction speed, high yield and mild conditions

Active Publication Date: 2011-07-20
四川弘远药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But in the last step of this invention, the F-C alkylation reaction is used, the reaction conditions are severe, and a large amount of aluminum trichloride is used

Method used

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  • Novel synthetic method of aripiprazole and intermediate thereof
  • Novel synthetic method of aripiprazole and intermediate thereof
  • Novel synthetic method of aripiprazole and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) Preparation of formula (I) compound 6-(4'-bromobutoxy)-1-indanone

[0033] Add 20g of 6-hydroxy-1-indanone, 58g of 1,4-dibromobutane, 18.4g of potassium carbonate, and 200ml of ethanol into a 500ml three-neck flask, reflux and stir for 3hrs, and TLC detects that the reaction is complete. Ethanol is distilled off, and 200ml of petroleum ether is added , stirred and crystallized for 3 hours, filtered out the solid, washed with a large amount of water, drained as much as possible, and dried at 40°C to obtain 30.0 g of compound 6-(4'-bromobutoxy)-1-indanone of formula (I). The rate is 79%. The proton nuclear magnetic resonance spectrum of formula (I) compound is as figure 1 shown.

[0034] Melting point: 56-57°C

[0035] 1 H NMR (300MHz, CDCl 3 )δ1.92~1.97(m, 2H), 2.02~2.10(m, 2H), 2.67~2.71(m, 2H), 3.05(t, J=6.0Hz, 2H), 3.47(t, J=6.4Hz , 2H), 4.00(t, J=5.9Hz, 2H), 7.14~7.18(m, 2H), 7.33~7.36(m, 1H).

[0036] (2) Preparation of formula (II) compound 6-[4'-[4"-(2...

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Abstract

The invention relates to a new method for synthesizing Aripiprazole and an intermediate thereof. The method of the invention adopts 6-hydroxy-1-indanone as a raw material to react with 1, 4-dibromobutane, 1-(2, 3-dichlorophenyl)piperazine or hydrochlorides thereof, and to be oximated to generate the intermediate then to be subjected to rearrangement by Beckmann to generate target compound Aripiprazole. The method has the advantages of short synthesizing route, moderate reaction conditions, simple operation, fast reaction, high yield and being in favor of industrialized production. Concretely,the intermediate for preparing the Aripiprazole of the invention is 6-[4'-[4''-(2''', 3'''-dchlorophenyl)-1''-piperazidine]-butoxy]-1-indeneoxime.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a method for synthesizing antipsychotic drug Aripiprazole. Background technique [0002] Aripiprazole, 7-{4'-[4"-(2"',3"'-dichlorophenyl)-1"-piperazine]butoxy}-3,4-dihydro-2( The structural formula of 1H)-quinolone is: [0003] [0004] Aripiprazole belongs to atypical antipsychotic drugs, used for the treatment of various acute and chronic schizophrenia and bipolar affective disorder, developed by Otsuka Pharmaceutical Company of Japan. Aripiprazole was launched in the United States in 2002 for the treatment of schizophrenia. According to Chinese patent application CN1450056A, the method for preparing aripiprazole involved in this application has long reaction time, low yield, cumbersome post-processing, and the use of a highly toxic solvent such as chloroform, which is not conducive to industrial production. There are many researches on aripiprazole recently in China, among which...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/20C07D295/135
Inventor 秦欣荣徐开辉刘华
Owner 四川弘远药业有限公司