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Preparation method of 2-piperidinecarboxylic acid, 3-piperidinecarboxylic acid and 4-piperidinecarboxylic acid

A technology of piperidinecarboxylic acid and picolinic acid, applied in organic chemistry and other directions, can solve the problems of complicated solid waste treatment, high catalyst price, long reaction route, etc. Effect

Inactive Publication Date: 2011-09-07
CHANGZHOU DAOU CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The object of the present invention is a kind of preparation method of 2-piperidine carboxylic acid, 3-piperidine carboxylic acid and 4-piperidine carboxylic acid, to overcome the defective that the above-mentioned prior art exists, promptly overcome the reaction scheme when preparing 2-piperidine carboxylic acid. It overcomes the shortcomings of high catalyst price and easy passivation by alkali when preparing 3-piperidinecarboxylic acid, overcomes the defects of high reaction operating pressure and complicated solid waste treatment when preparing 4-piperidinecarboxylic acid, and provides piperidine Formic acid is common, more conducive to the synthetic method of industrial operation

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Hydrogenation reaction

[0025] Autoclave nitrogen pressure test to more than 2Mpa, after ensuring that there is no leakage in the autoclave, drop 600g 2-pyridinecarboxylic acid, 3600ml water, add 30g palladium carbon catalyst (palladium content 5%) under the protection of nitrogen, airtight autoclave, replace with nitrogen three times , replaced by hydrogen twice, to ensure that there is no oxygen in the kettle, pass hydrogen to 3.5Mpa, raise the temperature to 80°C, start the hydrogen absorption reaction, react for about 3 hours, stop hydrogen absorption, gradually increase the temperature to 100°C, reduce the hydrogen pressure Add to 5Mpa, continue the hydrogenation reaction under this condition, until no hydrogen is absorbed, sample analysis, thin layer chromatography, using a chromatographic plate coated with silica gel G, the developer is 95% ethanol, after development, dry in the air. When developing color with iodine vapor, there should be no 2-picolinic aci...

Embodiment 2

[0029] (1) Hydrogenation reaction

[0030] The nitrogen pressure of the autoclave is tested to above 2Mpa to ensure that there is no leakage in the autoclave. Drop into 20kg 4-pyridinecarboxylic acid, 160kg water and 0.4kg palladium charcoal catalyst (palladium content 5%) in batching kettle, after dissolving and diluting, autoclave is vacuumized, and the material in batching kettle is sucked in autoclave, closes vacuum, uses Nitrogen replacement three times, hydrogen replacement twice, to ensure that there is no oxygen in the kettle, hydrogen is introduced, the pressure is controlled at 3-4Mpa, the temperature is slowly raised to 80°C, and the hydrogen absorption reaction starts. After about 3 hours of reaction, the hydrogen absorption stops and gradually increases. The temperature was raised to 100°C, and the hydrogen pressure was increased to 5Mpa. Under this condition, the reaction was maintained for 3 hours until no hydrogen was absorbed. Samples were analyzed and plated ...

Embodiment 3

[0034] (1) Hydrogenation reaction

[0035] The nitrogen pressure of the autoclave is tested to above 2Mpa to ensure that there is no leakage in the autoclave. Drop into 100kg 4-pyridinecarboxylic acid, 500kg water and 1kg palladium carbon catalyst (palladium content 5%) in batching still, after dissolving and diluting, autoclave is evacuated, and the material in the batching still is sucked in the autoclave, closes vacuum, with nitrogen Substitute three times, replace with hydrogen twice, ensure anaerobic conditions in the kettle, feed hydrogen, control the pressure at 3-4Mpa, slowly raise the temperature to 90°C, start the hydrogen absorption reaction, react for about 3 hours, stop the hydrogen absorption, and gradually increase the temperature To 95°C, increase the hydrogen pressure to 5Mpa, and keep the reaction under this condition for 3 hours until no hydrogen is absorbed, take a sample and analyze the spot plate until there is no raw material (no fluorescence indicates t...

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Abstract

The invention discloses a preparation method of 2-piperidinecarboxylic acid, 3-piperidinecarboxylic acid and 4-piperidinecarboxylic acid. The method is as follows: 2-pyridinecarboxylic acid, 3-pyridinecarboxylic acid and 4-pyridinecarboxylic acid are used as the raw material respectively, hydrogen is used to reduce the raw material to the corresponding piperidinecarboxylic acid in the presence of palladium-carbon catalyst. The method has the advantages of simple route, less side reactions, low hydrogenation pressure and hydrogenation temperature, short hydrogenation time and simple treatment of solid wastes, and is easy to realize industrialization.

Description

technical field [0001] The invention relates to a preparation method of 2-piperidinecarboxylic acid, 3-piperidinecarboxylic acid and 4-piperidinecarboxylic acid, and belongs to the technical field of synthesis and preparation of organic chemicals. Background technique [0002] 2-piperidinecarboxylic acid, 3-piperidinecarboxylic acid and 4-piperidinecarboxylic acid are important intermediates for the synthesis of various chiral drugs and biologically active substances. in: [0003] 2-piperidinecarboxylic acid is an important rigid cyclic non-protein amino acid, which can not only limit the conformation of polypeptides, but also serve as a multifunctional backbone in the synthesis library of different compounds, so it is widely used in many chiral drugs and biologically active substances preparation. For example, the local anesthetic ropivacaine and the antipsychotic drug thioridazine are all made from 2-piperidinecarboxylic acid as the main raw material. [0004] 3-piperid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/60C07D211/62C07D211/02
Inventor 葛青曹庆华蒙圣武
Owner CHANGZHOU DAOU CHEM IND
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