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A kind of synthetic method of n-(3-methoxypropyl)-4-aminopiperidine

A technology of methoxypropyl and aminopiperidine dihydrochloride, which is applied in the field of preparation of pharmaceutical intermediate compounds, can solve problems such as difficult filtration and difficult industrialization, and achieve easy handling and storage, simple operation and low price cheap effect

Active Publication Date: 2016-04-13
YOUCARE PHARMA GROUP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] This method uses lithium aluminum hydride, and the experimental operation requires an oxygen-free and water-free environment. It is not easy to filter during post-processing. Therefore, the industrialization of this method is difficult.

Method used

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  • A kind of synthetic method of n-(3-methoxypropyl)-4-aminopiperidine
  • A kind of synthetic method of n-(3-methoxypropyl)-4-aminopiperidine
  • A kind of synthetic method of n-(3-methoxypropyl)-4-aminopiperidine

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0060]

[0061] At room temperature, in a 250ml three-necked flask, add 17.1g N-(3-methoxypropyl)piperidone, 10.7g benzylamine, 100ml methanol, stir and dissolve, then add 21.2g triacetoxyhydroboration After adding sodium, after stirring at room temperature for 4 hours, the conversion was complete as monitored by TLC. Add 100ml of dilute hydrochloric acid with a concentration of 0.1mol / L to quench, evaporate the solvent under reduced pressure, add 100ml of water and 100ml of ethyl acetate, stir and separate, keep the organic layer, extract the aqueous layer twice with ethyl acetate, and combine the organic Mutually. The organic phase was washed twice with water, dried over anhydrous magnesium sulfate for 4 hours and concentrated to obtain 21.6 g of an oily product with a molar yield of 82.3%.

[0062] Example 2-5 is to screen the substituted benzylamine of this step reaction, and the charging ratio and experimental operation are all the same as Example 1, and the results a...

example 4

[0065] The concrete operation of example 4 is as follows:

[0066] At room temperature, in a 250ml three-necked flask, add 17.1g of N-(3-methoxypropyl)piperidone, 13.7g of p-methoxybenzylamine, and 100ml of methanol. After stirring and dissolving, add 21.2g of three After sodium acetoxyborohydride was stirred at room temperature for 4 hours, the conversion was complete as monitored by TLC. Add 100ml of dilute hydrochloric acid with a concentration of 0.1mol / L to quench, evaporate the solvent under reduced pressure, add 100ml of water and 100ml of ethyl acetate, stir and separate, keep the organic layer, extract the aqueous layer twice with ethyl acetate, and combine The organic phase. The organic phase was washed twice with water, dried over anhydrous magnesium sulfate for 4 hours and concentrated to obtain 23.2 g of an oily product with a molar yield of 88.6%.

[0067] Example 6-7 is to screen the solvent of this step reaction, and charging ratio and operation are identical...

example 11

[0072]

[0073] At room temperature, in a 250ml three-neck flask, add 13.1g of intermediate C-1 and 100ml of methanol, stir until dissolved, add 3g of 10% palladium carbon, pass in hydrogen under normal pressure, and react for more than 12 hours. After the conversion of raw materials is monitored by TLC , filter out the palladium carbon, add dropwise 100ml concentration of 2mol / L HCl ethanol solution to the filtrate, after a large amount of solids appear, continue to stir for more than 4 hours, filter to obtain a white solid, weigh 11.8g after drying, and the molar yield is 96.3%.

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Abstract

The present invention relates to a method for synthesizing a prucalopride key intermediate, and in particular, to a method for synthesizing N-(3-methoxylpropyl)-4-aminopiperidine, comprising reacting 1-(3-methoxylpropyl)piperidine-4-one with benzylamine substituted with a benzene ring to generate 1-(3-methoxylpropyl)-4-benzylaminopiperidine under the action of a reductant, and obtaining N-(3-methoxylpropyl)-4-aminopiperidine via catalysis of palladium-carbon.

Description

Technical field: [0001] The present invention relates to a preparation method of a pharmaceutical intermediate compound, in particular to a synthesis method of a prucalopride key intermediate: 1-(3-methoxypropyl)-4-aminopiperidine, the method Including 1-(3-methoxypropyl)piperidin-4-one and benzylamine substituted with benzene ring under the action of reducing agent to generate 1-(3-methoxypropyl)-4-benzylaminopiper Pyridine can be catalyzed by palladium carbon to obtain 1-(3-methoxypropyl)-4-aminopiperidine. Background technique: [0002] Chronic constipation (CC) is a common clinical digestive system disease with a high incidence, especially in women and the elderly. Although there are many drug and non-drug treatments for CC, the survey shows that patients are not satisfied with the curative effect, and its impact on quality of life and the resulting economic burden cannot be ignored. [0003] The structure of Prucalopride Succinate is as follows: [0004] [0005] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/58
CPCC07D211/58
Inventor 葛志敏武艳朋杨磊陈林
Owner YOUCARE PHARMA GROUP
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