High-purity blonanserin and preparation method thereof

A piperazinyl and fluorophenyl technology is applied in the field of drugs for treating schizophrenia, and achieves the effects of low cost, favorable industrial production, easy separation of products and high purity

Active Publication Date: 2009-09-16
AVENTIS PHARMA HAINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

I

Method used

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  • High-purity blonanserin and preparation method thereof
  • High-purity blonanserin and preparation method thereof
  • High-purity blonanserin and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add compound III163g, cyclooctanone 380g, cyclohexylamine 5g and RuH to a 2L three-necked flask 2 (PPh 3 ) 0.5g, heated to 160~170℃. The reaction was stirred for 5 hours, and the reaction was detected by TLC. After the reaction was completed, the temperature was lowered to 70° C., 100 ml of isopropanol was added, and the mixture was stirred while being naturally cooled to room temperature, suction filtered, and the filter cake was dried to a constant weight to obtain 211 g of the compound of formula II with a yield of 76%. Melting point: 236~239°C, HPLC purity 98%.

Embodiment 2

[0028] 200 g of compound II obtained above was removed, 300 ml of phosphorus oxychloride was added, and the mixture was heated and refluxed for 2 hours. After cooling to room temperature, 2L of chloroform was added to the mixture and washed with saturated sodium carbonate. The organic phase was separated, dried with anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified with isopropanol to obtain 154 g of solid product with a yield of 71%. Melting point: 111-112°C, HPLC purity 98%.

Embodiment 3

[0030] 140 g of compound III obtained above, 150 g of methylpiperazine, 50 g of sodium iodide and 2 L of toluene were mixed and refluxed for 12 hours, cooled to room temperature, and washed with saturated sodium carbonate. The organic phase was separated, dried with anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified with isopropanol to obtain 123 g of solid product with a yield of 78%. Melting point: 133-135°C, HPLC purity 99.5%.

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Abstract

The invention discloses a high-purity 2-(4-ethyl-1-piperazinyl)-4-(4-fluorophenyl)-5, 6, 7, 8, 9, 10-hexahydro-cycloocta-(b) pyridine and a preparation method thereof. The target product of the invention can be applied to the treatment of schizophrenia, with higher safety and effectiveness. The preparation method has mild reaction condition and simple post treatment, and can obtain high-purity final products and is easier to implement industrialized production.

Description

Technical field [0001] The present invention relates to a high-purity stable 2-(4-ethyl-1-piperazinyl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydroaromatic Sino[b]pyridine and its preparation method can be used as drugs for treating schizophrenia. Background technique [0002] Blunanserin, chemical name: 2-(4-ethyl-1-piperazinyl)-4-(4-fluorophenyl)-5,6,7,8,9,10-hexa Hydrogen octano[b]pyridine. It is a medicine for the treatment of psychiatric diseases and can be used to treat schizophrenia. Its chemical structure is shown in the following formula: [0003] [0004] EP0385237 discloses a common method for preparing compounds of formula I, and the reaction route is as follows: [0005] [0006] In the first step reaction of the above route, polyphosphoric acid is used as a catalyst for the ring-closure reaction. The amount of polyphosphoric acid is 10 times that of the reactants. The use of a large amount of polyphosphoric acid will bring great difficulties to the post-reaction tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/04A61P25/18
Inventor 张海平
Owner AVENTIS PHARMA HAINAN
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