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New method for synthesizing levocetirizine and key intermediate thereof

A technology of levocetirizine and compound, applied in the field of new intermediates, key intermediates for synthesizing levocetirizine, can solve the problems of unsatisfactory purity and yield of levocetirizine and the like

Inactive Publication Date: 2013-04-17
HUNAN JIUDIAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But according to this method, the purity and yield of levocetirizine in the industrialization process are unsatisfactory

Method used

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  • New method for synthesizing levocetirizine and key intermediate thereof
  • New method for synthesizing levocetirizine and key intermediate thereof
  • New method for synthesizing levocetirizine and key intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1, the preparation of N,N-dihydroxyethyl p-nitrobenzamide

[0068] Add 75g of dichloromethane, 30g of sodium carbonate, 12g of diethanolamine, and 3g of sodium sulfate into the reaction vessel, cool down to -5-0°C while stirring, and then slowly add 15g of p-nitrobenzoyl chloride. React for 2.5 hours, filter, add 100 g of water to dissolve the filter cake, and extract twice with 40 g of dichloromethane; combine the organic phases, add sodium sulfate to dry, filter and concentrate under reduced pressure to obtain the title compound.

Embodiment 2

[0069] Embodiment 2, the preparation of N, N-bis (2-chloroethyl) p-nitrobenzamide

[0070] Add 90 g of dichloromethane to the product obtained in Example 1, lower the temperature to -5-0° C. under stirring, add thionyl chloride dropwise, and react for 1 hour after the drop is complete, then add 250 g of 10% sodium bicarbonate solution, and divide The organic phase was taken, washed with 20 g of saturated brine, dried, filtered and concentrated under reduced pressure to obtain the title compound.

Embodiment 3

[0071] Embodiment 3, the preparation of (-)-1-[(4-chlorophenyl) benzyl]-4-p-nitrobenzoylpiperazine

[0072] Put 20 g of the product obtained in Example 2 into a reaction vessel, add 10 g of diisopropylethylamine and 1 g of sodium iodide, then stir the mixture and raise the temperature to 100-110 ° C, keep it warm for 2 hours, and add R (-)-4 chlorobenzhydrylamine 10g, keep warm for 10 hours after dripping, concentrate under reduced pressure, recover diisopropylethylamine, then add methanol 45g, reflux reaction at about 65°C for 3 hours, then cool to 5 -10°C, filter, wash the filter cake with methanol first, then wash with water, and dry to obtain the title compound.

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PUM

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Abstract

The invention provides a new compound, namely a compound as shown in formula (IV), wherein R refers to Cl, Br, NO2, OH and OR ', and R' refers to alkyl. The invention further provides application of the new compound in synthesis of levocetirizine, including application in synthesis for preparing (-)-1-((4-chlorphenyl)benzyl) piperazine, as well as application as an intermediate for synthesis of the levocetirizine. The invention further provides compounds (II) and (III) which can be used in the synthesis process of the compound (IV).

Description

field of invention [0001] The invention belongs to the field of chemical medicines, and relates to a new method for preparing (-)-1-[(4-chlorophenyl)benzyl]piperazine, a key intermediate for synthesizing levocetirizine, and a method for the preparation of levocetirizine. Novel intermediates in the process described. Background technique [0002] Levocetirizine was launched in February 2001. It is a third-generation antiallergic drug. Since it is the L-form of cetirizine, its pharmacological effects are similar to those of cetirizine. It is mainly used to treat the respiratory system, skin and eyes. Allergic diseases in other places, such as allergic rhinoconjunctivitis, allergic skin diseases, allergic asthma, etc., have quick onset, strong and long-lasting effects, but avoid the sedative and lethargic effects of cetirizine on the central nervous system. side effect. [0003] [0004] (-)-1-[(4-chlorophenyl) benzyl]piperazine is an important intermediate for the synthes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/192C07D295/073C07D295/088C07C233/69C07C235/48C07C233/66C07C235/46C07C231/12
Inventor 朱志宏谭军华卜振军郑霞辉杨静
Owner HUNAN JIUDIAN PHARMA
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