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Preparation method for escitalopram oxalate

A technology of escitalopram oxalate and toluyl tartrate, which is applied in the field of medicine, can solve the problems of expensive and difficult to obtain, low yield, harsh reaction conditions, etc., and achieve easy separation and purification, high yield, The effect of easy access to raw materials

Active Publication Date: 2012-02-01
山东安信制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods also have the problems of using expensive and difficult-to-obtain reagents, harsh reaction conditions and low yields.

Method used

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  • Preparation method for escitalopram oxalate
  • Preparation method for escitalopram oxalate
  • Preparation method for escitalopram oxalate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Dissolve 70.0g (0.13mol) of D-di-p-methylbenzoyl tartrate of S-type diol in 650ml of purified water, add 65ml (0.13mol) of 2mol / L sodium hydroxide solution, and control the temperature at 20±5°C Stir for 0.5 hours; after the reaction is complete, add 27.4 g (0.14 mol) of p-toluenesulfonyl chloride under control of the system temperature at 0-5° C., then add 90 ml (0.18 mol) of 2 mol / L sodium carbonate solution dropwise, and complete the dropwise addition in 0.5 hours. After the dropwise addition, the temperature was controlled at 0-5°C and the reaction was stirred for 3 hours; then, sodium hydroxide solution was added to adjust the pH value to 12-13, and the aqueous phase was extracted three times with 300ml of dichloromethane, and the organic phase was combined and washed with 200ml of purified water Once, separate the liquid, add 12.6g (0.14mol) of oxalic acid, stir for 2 hours under temperature control at 20±5°C, cool to -5~5°C, filter, and dry at 50±5°C to obtain 49....

Embodiment 2

[0028] Dissolve 70.0g (0.13mol) of D-di-p-methylbenzoyl tartrate of S-type diol in 650ml of purified water, add 65ml (0.13mol) of 2mol / L sodium hydroxide solution, and control the temperature at 20±10°C Stir for 40 minutes; after the reaction is complete, add 27.4 g (0.14 mol) of p-toluenesulfonyl chloride under control of the system temperature at 0-5 ° C, and dropwise add 90 ml (0.18 mol) of 2 mol / L sodium hydroxide solution within 40 minutes, and control the temperature Stir and react at 0-5°C for 3 hours; then add sodium hydroxide solution to adjust the pH value to 12-13, extract the aqueous phase three times with 300ml dichloromethane, combine the organic phases, wash once with 200ml purified water, separate the liquid, add 12.6g (0.14mol) of oxalic acid, stirred at 20±10°C for 2 hours, cooled to -5~5°C, filtered, and dried at 50±5°C to obtain 48.1g of white powdery solid, yield 88.8%, mp: 148.9-149.4°C.

Embodiment 3

[0030] Dissolve 70.0g (0.13mol) of D-di-p-methylbenzoyl tartrate of S-type diol in 650ml of purified water, add 65ml (0.13mol) of 2mol / L sodium hydroxide solution, and control the temperature at 20±10°C Stir at down for 0.5 hour; After the reaction is complete, add 27.4g (0.14mol) of p-toluenesulfonyl chloride under the control system temperature at 0-5°C, add 90ml (0.18mol) of 2mol / L sodium carbonate solution dropwise within 50 minutes, and control the temperature at 0 Stir and react at -5°C for 2.0 hours; then add sodium hydroxide solution to adjust the pH to 12-13, extract the aqueous phase three times with 300ml dichloromethane, combine the organic phases, wash once with 200ml purified water, separate the liquids, and add oxalic acid 12.6g (0.14mol), stirred at 20±10°C for 2 hours, cooled to -5~5°C, filtered, and dried at 50±5°C to obtain 48.5g of white powdery solid, yield 89.5%, mp: 149.9 -150.4°C.

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Abstract

The invention discloses a preparation method for escitalopram oxalate, which is characterized in that D-toluoyl tartrate of S-diol is dissolved into water, and sodium hydroxide is used for neutralization to obtain free S-diol; then, the temperature is controlled to be 0 to 10 DEG C, paratoluensulfonyl chloride is added, then, inorganic alkaline solution is dripped, and the ring closure reaction is carried out after the reaction for 2 to 4 hours; after the reaction is completed, the pH value is regulated to 12 to 13, and then, the extraction, the water washing and the liquid separation are carried out; and after oxalic acid is added for salt forming, the temperature reduction, the filtering and the drying are carried out, and products are obtained. In the ring closure reaction, water is adopted as solvents, the condition is mild, the environment is friendly, byproducts of each step of reaction in the synthesis method are few, the yield is high, in addition, products in each step of reaction are easy to separate and purity, raw materials used in the synthesis method are easy to obtain, the operation is simple, and the industrial production is easy.

Description

technical field [0001] The invention relates to a preparation method of escitalopram oxalate, which belongs to the technical field of medicine. Background technique [0002] Escitalopram (escitalopram) is a known antidepressant that has been on the market for many years. At present, the main product in the market is escitalopram oxalate (as shown in structural formula I), and the trade name is Lycep. Escitalopram oxalate has a highly selective inhibitory effect on the reuptake of serotonin (5-HT), with little effect on the reuptake of norepinephrine and dopamine. It increases the concentration of 5-HT in the synaptic cleft by preventing 5-HT reabsorption, thereby producing antidepressant effects. [0003] [0004] The main preparation method of escitalopram reported so far is to obtain it through ring closure of the intermediate S-type diol (shown in structural formula II). [0005] [0006] In US Pat. No. 4,650,884, racemic diol is reacted in 70% concentrated sulfur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/87C07C55/07C07C51/41
Inventor 周先国杨庆坤张雷雷李昌瑜吴柯张兆珍董廷华
Owner 山东安信制药有限公司
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