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Process for preparing piperidine derivative

A compound and chemical structure technology, applied in the field of preparation of piperidine derivatives, can solve the problems of not obtaining the target product, difficult product purification, cumbersome operation, etc.

Inactive Publication Date: 2006-11-22
BEIJING SIHUAN KEBAO PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method is cumbersome to operate, and the resulting product is difficult to purify, and column chromatography is required to obtain a qualified product
[0012] In U.S. Patent No.5407941, a reduction method using lithium aluminum hydride as a reducing agent in tetrahydrofuran solution was introduced, but the experimental verification was carried out according to this method, and the target product was not obtained as a result

Method used

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  • Process for preparing piperidine derivative
  • Process for preparing piperidine derivative
  • Process for preparing piperidine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Under the protection of nitrogen, 150 ml of tetrahydrofuran and 50 ml of toluene were added to a 500 ml three-necked flask, and 15.0 g of vacuum-dried amide was added with stirring, and the temperature was lowered to 0° C. with an ice-salt bath. Take 18 milliliters of sodium dihydroaluminate (Red-Al), dilute it with 15 milliliters of toluene, add it dropwise into the reaction flask, after the addition is complete, stir for 36 hours. After the reaction was completed, 10 ml of water was added dropwise under an ice-water bath, stirred for 3 hours, filtered with suction, the filter cake was washed twice with tetrahydrofuran, and the filtrates were combined to remove the solvent under reduced pressure to obtain a brown-red viscous substance. Add toluene to dissolve, wash with dilute acid and dry. The desiccant was filtered off, the solution was precipitated, and solidified to obtain 8.7 g of the target compound. Yield: 60%.

[0024] HPLC purity: 98.5%.

Embodiment 2

[0026] Under the protection of nitrogen, 300 ml of tetrahydrofuran and 100 ml of toluene were added to a 1000 ml three-neck flask, 30.0 g of vacuum-dried amide was added under stirring, and the temperature was cooled to 0° C. with an ice-salt bath. Take 110 ml of sodium dihydroaluminate (Red-Al), dilute it with 100 ml of toluene, and add it dropwise into the reaction flask. After the dropwise addition was completed, the mixture was naturally raised to room temperature and stirred overnight. After the reaction was completed, 40 ml of water was added dropwise in an ice-water bath, stirred for 4 hours, filtered with suction, and the filter residue was washed twice with tetrahydrofuran, and the filtrates were combined to remove the solvent under reduced pressure to obtain a brown-red sticky substance. Add toluene to dissolve, wash with dilute acid and dry. The desiccant was filtered off, the solution was removed and solidified to obtain 20.2 g of the target compound. Yield: 70%....

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Abstract

The invention provides a process for preparing Rupatadine or its salts, wherein the Rupatadine has a chemical formula (I).

Description

field of invention [0001] The invention relates to a preparation method of an antiallergic drug rupatadine or a salt thereof. Background of the invention [0002] Rupatadine, as a dual antagonist of histamine and platelet aggregation, was launched in Europe in 2003 and is used in the treatment of allergic rhinitis and hay fever, and has broad market prospects. Rupatadine has the chemical structure of the following formula (I). [0003] [0004] Rupatadine can be synthetically prepared from two synthetic routes using desloratadine as a starting material: [0005] [0006] Route 1 [0007] [0008] route 2 [0009] Among the above two routes, the yield of route 1 is low, the reaction is difficult to control, and it is difficult to obtain a purer product. [0010] The key synthetic step in Route 2 is the reduction of amides. In published literature reports, there are the following two methods for reducing amide compounds...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D211/26C07D213/36C07D221/06
Inventor 曲峰王玉生
Owner BEIJING SIHUAN KEBAO PHARM CO LTD
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