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Preparation method of high-purity cis-3,5-dimethylpiperidine

A technology of dimethylpiperidine and lutidine, which is applied in the field of preparation of high-purity cis-3,5-dimethylpiperidine, can solve problems such as the complex ratio of cis, and achieve high commercial value and process Simple, high product purity effect

Active Publication Date: 2017-07-04
VALIANT CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] It is relatively complicated to increase the cis ratio in the existing technology, so industrial production urgently needs to find a simple and suitable catalytic method and a simple and effective purification method to obtain high-purity cis-3,5-dimethylpiperidine

Method used

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  • Preparation method of high-purity cis-3,5-dimethylpiperidine
  • Preparation method of high-purity cis-3,5-dimethylpiperidine

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Embodiment 1

[0039] Add 645.0g of 3,5-lutidine, 77.4g of neutral alumina, 12.9g of potassium carbonate, and 25.8g of ruthenium on carbon (5% effective content) into a 2L autoclave. Close the autoclave, replace with nitrogen 6 times, and replace with hydrogen 6 times. After charging and heating to a hydrogen pressure of 9.0MPa and 150°C, the hydrogen pressure will drop significantly during the reaction process. The heat-preservation and pressure-holding reaction lasts for 5.0 hours, and the complete reaction of 3,5-lutidine is detected. The reaction crude product is obtained by suction filtration. The rate is 96.8%. Gas chromatography analysis showed that the purity of cis-3,5-dimethylpiperidine was 84.5%, and the purity of trans-3,5-dimethylpiperidine was 15.2%.

[0040] The 2L three-necked bottle is equipped with a mechanical stirrer, a thermometer, and a drying tube. Add the above reaction crude product, 340.0g n-hexane, and 35.0g absolute ethanol into a 2L three-necked flask. After r...

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Abstract

The invention relates to a preparation method of high-purity cis-3,5-dimethylpiperidine, and belongs to the field of organic synthesis. According to the preparation method, 3,5-dimethyl pyridine is taken as a raw material, a 3,5-dimethylpiperidine crude product is obtained via catalytic hydrogenation, and high-purity cis-3,5-dimethylpiperidine is obtained via precipitation purifying, wherein the cis gas chromatographic purity is larger than 99.5%. in the preparation method, neutral aluminium oxide and an alkali are introduced, and the combination mode of pyridine molecules with catalyst molecules in hydrogenation process is changed, so that it is beneficial for formation of cis-form products, and the crude product which can be applied in drug production directly is obtained; the cis-isomeride with a purity higher than 99.5% after treatment is obtained for the first time in the field of cis synthesis and separation of 3,5-dimethylpiperidine, and great referential significance and relatively high commerical value in the fields of synthesis purification and industrialized production of piperidine derivatives are achieved.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of high-purity cis-3,5-dimethylpiperidine. Background technique [0002] Cis-3,5-dimethylpiperidine is a derivative of piperidine, which is widely used in the preparation of antifungal agents and plant growth regulators. [0003] Cis-3,5-dimethylpiperidine is also used as an intermediate to prepare aminomethylheterocyclic insecticide compounds and compounds that can regulate eating behavior and related diseases, including obesity, Diabetes, cancer (tumours), inflammatory diseases, depression, stress-related diseases and Alzheimer's disease. In addition, cis-3,5-dimethylpiperidine is also very useful in the preparation of carbon-20-dihydro-dehydro-(cyclic amino) derivatives of macrolide antibiotics and in the preparation of molecular sieves. [0004] There are two existing methods for synthesizing 3,5-dimethylpiperidine: furanamine method and hyd...

Claims

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Application Information

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IPC IPC(8): C07D211/12
CPCC07B2200/09C07D211/12
Inventor 孙虎姜春晓付文岗孙晟源迟鹏利迟乃乔
Owner VALIANT CO LTD
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