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Method for regulating and controlling catalytic hydrogenation reaction of pyridine derivative with redox potential

A technology of catalytic hydrogenation and potential regulation, which is applied in the direction of organic chemistry, can solve the problems of high production equipment requirements, low catalytic activity, high production cost, etc., and achieve the effects of shortening the test cycle, expanding the application range, and reducing screening costs

Inactive Publication Date: 2019-04-26
ANHUI DEXINJIA BIOPHARM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Commonly used metal catalysts for catalytic hydrogenation include nickel-based (Raney Ni), rhodium-based, ruthenium-based, palladium-based, etc. For the above reactions, the catalytic activity of nickel is low, and generally requires a high temperature above 200°C and a high pressure reaction above 10MPa. Higher requirements; rhodium-based catalysts have better effects, such as: Zhejiang Stellite Pharmaceutical Co., Ltd. uses 3-hydroxypyridine to prepare racemic 3-hydroxypiperidine through 5% rhodium carbon (Rh / C) catalytic hydrogenation, but The price of rhodium is relatively high (about 5 to 8 times that of ruthenium), its production cost is very high, and the pollution is relatively heavy

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  • Method for regulating and controlling catalytic hydrogenation reaction of pyridine derivative with redox potential
  • Method for regulating and controlling catalytic hydrogenation reaction of pyridine derivative with redox potential
  • Method for regulating and controlling catalytic hydrogenation reaction of pyridine derivative with redox potential

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Embodiment 1

[0037] In the present embodiment, the method for screening 4-hydroxypyridine catalytic hydrogenation reaction by means of ORP data is as follows:

[0038] 1. Dissolve 1.9g of 4-hydroxypyridine in 15-20mL of water, 30%-50% glacial acetic acid and 5-15% aqueous hydrochloric acid (V / V) to obtain a possible medium environment for the substrate to undergo catalytic hydrogenation reaction;

[0039] 2. The ORP of each of the above systems is tested separately, and based on the measurement results, 25% acetic acid, 40% acetic acid, 5% hydrochloric acid and 10% hydrochloric acid aqueous solution are selected for catalytic hydrogenation reaction. ;

[0040] 3. Dissolve 19g of 4-hydroxypyridine in about 200mL of acetic acid or hydrochloric acid aqueous solution, catalyze with 5% Ru / C, and add 5%, 10%, and 15% of the substrate mass; the hydrogen pressure in the reactor is controlled at 3-5MPa , temperature 80-100°C, when the hydrogen pressure no longer drops, take samples and monitor res...

Embodiment 2

[0045] In this embodiment, the method for screening the catalytic hydrogenation reaction of 3-hydroxypyridine derivatives with the help of ORP data is as follows:

[0046] 1. Dissolve 1.9g of 3-hydroxypyridine in 15-20mL of water, 30%-50% glacial acetic acid and 5-10% phosphoric acid aqueous solution (V / V) to obtain a possible medium system for the catalytic hydrogenation reaction of the substrate;

[0047] 2. The ORP of each of the above systems is detected separately; based on the measurement results, 35% acetic acid, 50% acetic acid and 10% phosphoric acid aqueous solution are selected for catalytic hydrogenation reaction;

[0048] 3. Dissolve 19g of 3-hydroxypyridine in about 200mL of acetic acid or phosphoric acid aqueous solution, catalyze with 5% Ru / C, add 10% and 15% of the substrate quality; the hydrogen pressure in the reactor is controlled at 3-5MPa, and the temperature is 70 -100°C, when the hydrogen pressure no longer drops, samples are taken and monitored respect...

Embodiment 3

[0053] In this embodiment, the method for screening the catalytic hydrogenation reaction of 2-picoline derivatives with the help of ORP data is as follows:

[0054] 1. Dissolve 1.88g of 2-picoline in 15-20mL of water, 30%-50% glacial acetic acid and 5-15% aqueous hydrochloric acid (V / V) to obtain a possible medium environment for the substrate to undergo catalytic hydrogenation reaction;

[0055] 2. The ORP of each of the above systems is detected separately; based on the measurement results, 35% acetic acid, 5% hydrochloric acid and 10% hydrochloric acid aqueous solution, which may have higher oxidation performance of 2-picoline, are selected for catalytic hydrogenation reaction;

[0056] 3. Dissolve 18.8g of 2-picoline in about 200mL of acetic acid or hydrochloric acid aqueous solution, catalyze with 5% Ru / C, add 5%, 10% of the substrate quality; the hydrogen pressure in the reactor is controlled at 2-4MPa, The temperature is 80-100°C, and when the hydrogen pressure no longe...

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Abstract

The invention discloses a method for regulating and controlling catalytic hydrogenation reactions of a pyridine derivative with redox potential. On the basis of data such as redox potential (ORP) andcatalytic hydrogenation reaction process of the pyridine derivative in different medium systems, a scheme that the catalytic hydrogenation reaction of the pyridine derivative is promoted by improvingpyridine derivative ORP with an acid water solution is proposed. As the catalytic hydrogenation reactions of the pyridine derivative are instructed with ORP data, the testing period is shortened, meanwhile, by adopting the process, the pressure of hydrogenation reactions can be reduced, a piperidine product has the advantages of being high in purity, convenient in aftertreatment, and the like, andthus great instruction significances can be achieved for industrial development of the pyridine derivative.

Description

technical field [0001] The invention relates to a catalytic hydrogenation reaction of pyridine derivatives, in particular to a method for regulating the catalytic hydrogenation reaction of pyridine derivatives by utilizing oxidation-reduction potential, and belongs to the field of preparation of pharmaceutical intermediates. Background technique [0002] Piperidine, piperidinol and their derivatives are an important class of pharmaceutical intermediates, which are widely used in the synthesis of diabetes drugs, antidepressants, antineoplastic drugs, local anesthetics and antihypertensive drugs. Among them, 3-hydroxypiperidine Pyridine is mainly used to synthesize the key intermediate of ibrutinib (S)-1-tert-butoxycarbonyl-3-hydroxypiperidine, and 4-hydroxypiperidine is mainly used to synthesize N-Boc-4-hydroxypiperidine, etc. Piperidine derivatives have a wide range of applications and broad market prospects in the pharmaceutical industry. [0003] At present, one of the mo...

Claims

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Application Information

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IPC IPC(8): C07D211/12C07D211/46C07D211/42
CPCC07D211/12C07D211/42C07D211/46
Inventor 许坤惠爱玲张文成吴泽宇陈天云汪志勇
Owner ANHUI DEXINJIA BIOPHARM
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