A kind of preparation method of pyridine derivative

A derivative, pyridine technology, applied in the field of preparation of pyridine derivatives, can solve problems such as complex process, high cost of raw materials, unfavorable environmental protection and industrial production

Active Publication Date: 2021-04-16
XINFA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The price of the raw material 4-aminopyridine is high, the electron cloud density of 4-aminopyridine is high, it is easy to be oxidized, and it is easy to produce viscous by-products. This method is not suitable for industrial production
[0037] In summary, the preparation methods of pyridine derivatives in the prior art have problems such as complex process, high cost of raw materials, low yield, unfavorable for environmental protection and industrial production.

Method used

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  • A kind of preparation method of pyridine derivative
  • A kind of preparation method of pyridine derivative
  • A kind of preparation method of pyridine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Embodiment 1: the preparation of 3,5-dichloropiperidin-4-one

[0064] In a 500 ml four-neck flask connected with stirring, a thermometer, and a reflux condenser, 200 g of chloroform, 27.1 g (0.2 moles) of piperidin-4-one hydrochloride, and chlorine gas were passed between 40-45 ° C, and a total of Chlorine 32.0 grams, 40-45 ° C stirring reaction for 5 hours, cooled to 20-25 ° C, nitrogen to blow off residual chlorine and by-product hydrogen chloride gas, blow off for 2 hours, add 50 grams of water, adjust pH with 20% sodium carbonate aqueous solution The value is 7-8, layered, the organic phase is washed once with 20 grams of saturated aqueous sodium chloride solution, layered, and the solvent is recovered by distillation to obtain 39.9 grams of light yellow liquid 3,5-dichloropiperidin-4-one, directly for relevant elimination reactions.

Embodiment 2

[0065] Embodiment 2: Preparation of 3,5-dibromopiperidin-4-one

[0066] In the 500 milliliter four-necked flask that is connected with stirring, thermometer, reflux condenser, 200 grams of chloroform, 13.6 grams (0.1 moles) piperidin-4-one hydrochloride, 41.0 grams (0.2 moles) 40% hydrobromic acid, Add 24.0 (0.21 moles) of 30% hydrogen peroxide dropwise at 30-35°C for about 2 hours, stir and react at 30-35°C for 3 hours, add 50 grams of water, adjust the pH value to 7-8 with 20% aqueous sodium carbonate solution, Separate the layers, wash the organic phase once with 20 g of saturated aqueous sodium chloride solution, separate the layers, and recover the solvent by distillation to obtain 29.2 g of yellow liquid 3,5-dibromopiperidin-4-one, which is directly used in related elimination reactions.

Embodiment 3

[0067] Embodiment 3: Preparation of 3,3,5-trichloropiperidin-4-one

[0068] In the 500 milliliter four-necked flask that is connected with stirring, thermometer, reflux condenser, 200 gram dichloromethanes, 27.1 gram (0.2 moles) piperidin-4-one hydrochloride, 43.0 grams (0.41 moles) 35% hydrochloric acid, Add 74.0 (0.65 mole) 30% hydrogen peroxide dropwise at 30-35°C for about 3 hours, after that, stir and react at 40-45°C for 3 hours, cool to 20-25°C, blow off residual chlorine and hydrogen chloride gas for 1 hour with nitrogen , add 50 grams of water, adjust the pH value to 7-8 with 20% aqueous sodium carbonate solution, separate layers, wash the organic phase once with 20 grams of saturated aqueous sodium chloride solution, separate layers, and recycle the solvent by distillation to obtain 47.4 grams of yellow liquid 3 ,3,5-Trichloropiperidin-4-one, directly used in related elimination reactions.

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Abstract

The invention relates to a preparation method of pyridine derivatives. The method uses piperidine-4-one hydrochloride as a raw material to obtain a series of pyridine derivatives through halogenation reaction and elimination reaction. Preparation of 3,5-dihalopiperidin-4-one and 3,3,5-trihalogenated piperidine-4 through halogenation reaction with piperidine-4-one hydrochloride and a specific amount of halogenated reagent -ketone or 3,3,5,5-tetrahalogenated piperidine-4-ketone, and then react with different types of basic reagents to obtain pyridine derivatives whose 4-position is respectively hydroxyl, amino or dimethylamino Elimination reaction. The invention has the advantages of simple and convenient operation, mild conditions, short process flow, low waste water volume, environmental protection and low cost, and is beneficial to the green industrialized production of the pyridine derivatives.

Description

technical field [0001] The invention relates to a preparation method of pyridine derivatives, in particular to pyridine derivatives 4-hydroxypyridine, 4-aminopyridine, 4-dimethylaminopyridine, 3-chloro-4-hydroxypyridine, 3-bromo-4-hydroxy Pyridine, 3-chloro-4-aminopyridine, 3-bromo-4-aminopyridine, 3,5-dichloro-4-hydroxypyridine, 3,5-dibromo-4-hydroxypyridine, 3,5-dichloro - The preparation method of 4-aminopyridine and 3,5-dibromo-4-aminopyridine belongs to the technical field of medicine and chemical industry. Background technique [0002] Hydroxypyridine (I1), also known as γ-pyridone (γ-pyridone), its English name is 4-hydroxypyridine, is an important organic synthesis intermediate, widely used in medicine, pesticides, etc., it is a synthetic It is an important raw material of pyridine sulfonamide diuretics (torasamide) and an important intermediate in the synthesis of efficient acylation catalyst DMAP. [0003] The synthetic method of 4-hydroxypyridine is seldom repor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/68C07D213/73C07D213/74
CPCC07D213/68C07D213/73C07D213/74
Inventor 鞠立柱戚聿新张明峰吕强三
Owner XINFA PHARMA
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