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Preparation method of levocetirizine

A technology of levocetirizine and compounds, which is applied in the field of preparation of levocetirizine, can solve problems such as long synthetic routes, and achieve the effects of short synthetic routes and high yields

Active Publication Date: 2020-04-03
湖南九典宏阳制药有限公司 +1
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

But this synthetic route is longer, in terms of (R)-4-chlorobenzhydrylamine, the total yield is 11%

Method used

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  • Preparation method of levocetirizine
  • Preparation method of levocetirizine
  • Preparation method of levocetirizine

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Embodiment 1

[0038] Step 1. Under nitrogen protection, 34.41g of 4-chlorobenzophenone and 48.17g of formamide were kept at 170-175°C until the raw material was less than 3% as detected by TLC / GC. The reaction system was added to 200g of water, and suction filtered. Wash the filter cake with water, dry the filter cake at 55°C, add 59.89g of 36% hydrochloric acid, 21.33g of absolute ethanol and 81.2g of water to the crude product and heat it to 75~80°C to reflux, check that the hydrolysis is complete, cool down to 25°C and suction filter, the filter cake Add water to form a paste, add sodium hydroxide and water to adjust the pH value to 10~11, add DCM to extract, wash the organic phase with saturated brine, dry over sodium sulfate and concentrate to obtain the compound of formula (III), which can be calculated by GC detection as shown in the figure , yield 80%, purity 98%,;

[0039] Formula (III);

[0040] Step 2. Add 23.00g of L-(+)-tartaric acid into a reaction flask containing 312.28g ...

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Abstract

The invention provides a preparation method of levocetirizine. The method comprises the following steps of: the step 1, carrying out a cyclization reaction on (R)-4-chlorodiphenyl methylamine and tris(2-chloroethyl)amine to obtain a compound represented by a formula (I); 2, performing condensation reaction of the compound shown in the formula (I) and 2-ethyl glycolate to obtain a compound shown ina formula (II); and the step 3, converting the compound shown in the formula (II) into levocetirizine. According to the preparation method, (R)-4-chlorodiphenyl methylamine and tris(2-chloroethyl)amine are taken as the initial raw materials, and cyclization reaction, condensation reaction and hydrolysis reaction are carried out so as to obtain levocetirizine. The synthetic route provided by the invention is short, the yield is high, and experimental results show that the yield of the levocetirizine prepared by the method provided by the invention can reach 47%, and the purity can reach 99.7%.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, in particular to a preparation method of levocetirizine. Background technique [0002] Levocetirizine hydrochloride, also known as levocetirizine hydrochloride, chemical name: (-)-[2-[4-(R)-4-chlorophenyl-benzyl-1-piperazine Base] ethoxy] acetic acid dihydrochloride; CAS registration number is 130018-87-0; English common name is levocetirizine dihydrochloride. Its structural formula is as follows: [0003] [0004] Levocetirizine hydrochloride is the third generation H 1 Receptor antagonist, listed in Germany for the first time in February 2001, trade name Xyzal, levocetirizine hydrochloride is the R-type optical isomer of cetirizine hydrochloride, overcomes the cetirizine hydrochloride in clinical practice The central nervous system side effects such as drowsiness and sedation caused by the S-type optical isomer in Lizine are used for the treatment of allergic diseases of the r...

Claims

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Application Information

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IPC IPC(8): C07D295/088
CPCC07B2200/07C07D295/088
Inventor 谭军华胡矿
Owner 湖南九典宏阳制药有限公司
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