A kind of method for preparing citalopram and s-citalopram

A technology of organic solvent and arylsulfonyl chloride, applied in the field of preparing citalopram and S-citalopram, can solve the problems of low solvent recovery rate, large environmental pollution and high production cost, and achieve simple post-processing and high yield , the effect of increasing productivity

Active Publication Date: 2021-06-29
ZHEJIANG HUAHAI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This kind of solvent has high solubility to raw materials and products, but it has high toxicity and low boiling point, which leads to low solvent recovery rate, high production cost and great environmental pollution.

Method used

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  • A kind of method for preparing citalopram and s-citalopram
  • A kind of method for preparing citalopram and s-citalopram
  • A kind of method for preparing citalopram and s-citalopram

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 34.2g of diol compound (II) and 100ml of methyl isobutyl ketone into a four-neck flask, stir to dissolve at room temperature, add 12g of NaOH, add 50ml of water, cool to 3°C, and slowly add 100ml of methyl alcohol A solution in which 27 g of p-toluenesulfonyl chloride was dissolved in isobutyl ketone was heated up to room temperature after the reaction was completed at 3°C. The layers were allowed to stand, and the aqueous layer was extracted once with 70ml of methyl isobutyl ketone; the combined organic layers were washed twice with 100ml of water each time. The yield of citalopram obtained by concentrating the organic layer was 83%, and the HPLC analysis result showed that the product had a purity of 99.6%.

Embodiment 2

[0027] Add 34.2g of S-diol compound (II') into the four-neck flask, add 100ml of methyl isobutyl ketone, stir at room temperature to dissolve, add 12g of NaOH, add 50ml of water, cool to 3°C, and then slowly dropwise add A solution of 27 g of p-toluenesulfonyl chloride was dissolved in 100 ml of methyl isobutyl ketone, and after the reaction was completed at 3° C., the temperature was raised to room temperature. The layers were allowed to stand, and the aqueous layer was extracted once with 70ml of methyl isobutyl ketone; the combined organic layers were washed twice with 100ml of water each time. The yield of S-citalopram (I') obtained by concentrating the organic layer was 85%, and the HPLC analysis results showed that the product had a purity of 99.8%.

Embodiment 3

[0029] Add 34.2g of diol compound (II) and 100ml of methyl isobutyl ketone into a four-neck flask, stir to dissolve at room temperature, add 12g of NaOH, add 50ml of water, cool to 3°C, and slowly add 100ml of A solution in which 16 g of methanesulfonyl chloride was dissolved in methyl isobutyl ketone was heated up to room temperature after the reaction was completed at 3°C. The layers were allowed to stand, and the aqueous layer was extracted once with 70ml of methyl isobutyl ketone; the combined organic layers were washed twice with 100ml of water each time. The yield of citalopram obtained by concentrating the organic layer was 80%, and HPLC analysis showed that the product had a purity of 99.5%.

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PUM

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Abstract

The present invention relates to diol compound (II) or S-diol compound (II ') in C 4 -C 7 In the mixed solvent of ketone solvent and water, under alkaline condition, react cyclization with arylsulfonyl chloride or alkylsulfonyl chloride to obtain citalopram and S-citalopram. The solvent used in the invention has high solubility to reactants and products, thus reducing the amount of solvent used and improving production capacity, and at the same time, the post-treatment extraction effect is good and the operation is simple and convenient.

Description

technical field [0001] The invention relates to a method for industrially preparing citalopram and S-citalopram. Background technique [0002] Citalopram, whose chemical name is 1-[3-(dimethylamino)propyl]-1-(4'-fluorophenyl)-1,3-dihydro-5-cyanoisobenzofuran, is a A new drug for the treatment of depression, it belongs to the selective serotonin reextraction inhibitors. Specifically as shown in structural formula I. Its S-configuration is the main active ingredient, also known as S-citalopram, and its specific structural formula is shown in formula I'. [0003] [0004] The synthetic method reported in the literature generally uses diol compound (II) and S-diol compound (II') as starting materials, under alkaline conditions, reacts with substituted sulfonyl chloride compounds, in organic solvent and water mixed solution Among them, the target product citalopram (I) or S-citalopram (I') is obtained through esterification and cyclization. The organic solvents used in the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/87
CPCC07D307/87
Inventor 梁尊俊肖伟烽黄文锋胡斯琪彭才华
Owner ZHEJIANG HUAHAI PHARMA CO LTD
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