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Preparation method of pyridine derivative

A derivative and pyridine technology, applied in the field of preparation of pyridine derivatives, can solve the problems of high electron cloud density of 4-aminopyridine, unfavorable environmental protection and industrial production, and high price of 4-aminopyridine, and achieves less waste and low cost. , the effect of short process flow

Active Publication Date: 2019-11-22
XINFA PHARMA
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  • 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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  • Preparation method of pyridine derivative
  • Preparation method of pyridine derivative
  • 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, which comprises the following steps: by using piperidine-4-ketone hydrochloride as a raw material, carrying out halogenation reaction and elimination reaction to obtain a series of pyridine derivatives. Piperidine-4-ketone hydrochloride and a specific amount of a halogenation reagent are subjected to a halogenation reaction torespectively prepare 3,5-dihalogenated piperidine-4-one, 3,3,5-trihalogenated piperidine-4-one, or 3,3,5,5-tetrahalogenated piperidine-4-one; then performing elimination reaction on the raw materialsand different types of alkaline reagents to obtain pyridine derivatives of which the 4-positions are hydroxyl, amino or dimethylamino groups respectively. The method is simple and convenient to operate, mild in condition, short in technological process, low in wastewater amount, environmentally friendly and low in cost, and green industrial production of the pyridine derivative is facilitated.

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 Applications(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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