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Method for preparing 3-hydroxypiperidine through liquid phase catalytic hydrogenation of 3-hydroxypyridine

A technology of hydroxypyridine liquid and hydroxypiperidine is applied in the field of liquid-phase catalytic hydrogenation of 3-hydroxypyridine to prepare 3-hydroxypiperidine, which can solve the problems of undiscovered 3-hydroxypiperidine research and reports, etc., and achieves cost Inexpensive, high-yield, high-quality effects

Inactive Publication Date: 2015-06-24
XIAN CATALYST NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Up to now, there has been no report on the use of ruthenium carbon as a catalyst for the preparation of 3-hydroxypiperidine

Method used

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  • Method for preparing 3-hydroxypiperidine through liquid phase catalytic hydrogenation of 3-hydroxypyridine

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Embodiment 1

[0021] The method for preparing 3-hydroxypiperidine by liquid-phase catalytic hydrogenation of 3-hydroxypyridine in this embodiment comprises the following steps:

[0022] Step 1. Add 50g of 3-hydroxypyridine, 1.0g of ruthenium carbon catalyst with 5% ruthenium mass content and 200mL of pure water into the autoclave, first adopt the method of feeding nitrogen to get rid of the air in the autoclave, and then use The method of feeding hydrogen is used to get rid of the nitrogen in the autoclave;

[0023] Step 2. Heat the autoclave after nitrogen removal in step 1, and at the same time, continue to feed hydrogen into the autoclave, and make 3-hydroxypyridine catalyze in liquid phase under the conditions of temperature of 140°C and pressure of 4.0MPa Hydrogenation reduction reaction, after 13 hours of reaction, stop feeding hydrogen, filter and recover the ruthenium carbon catalyst after natural cooling, carry out vacuum distillation on the filtered filtrate at a temperature of 67...

Embodiment 2

[0026] The method for preparing 3-hydroxypiperidine by liquid-phase catalytic hydrogenation of 3-hydroxypyridine in this embodiment comprises the following steps:

[0027] Step 1. Add 100g 3-hydroxypyridine, 2.0g ruthenium carbon catalyst with 5% ruthenium mass content and 200mL pure water into the autoclave, first adopt the method of feeding nitrogen to get rid of the air in the autoclave, and then use The method of feeding hydrogen is used to get rid of the nitrogen in the autoclave;

[0028] Step 2. Heat the autoclave after nitrogen removal in step 1, and at the same time, continue to feed hydrogen into the autoclave, and make 3-hydroxypyridine catalyze in liquid phase under the conditions of temperature of 140°C and pressure of 4.0MPa Hydrogenation reduction reaction, after 14 hours of reaction, stop feeding hydrogen, filter and recover the ruthenium carbon catalyst after natural cooling, carry out vacuum distillation on the filtered filtrate at a temperature of 67°C-69°C ...

Embodiment 3

[0031] The method for preparing 3-hydroxypiperidine by liquid-phase catalytic hydrogenation of 3-hydroxypyridine in this embodiment comprises the following steps:

[0032] Step 1, 150g 3-hydroxypyridine, 4.5g ruthenium mass content is 5% ruthenium charcoal catalyst and 450mL pure water are added in the autoclave, first adopt the method for feeding nitrogen to get rid of the air in the autoclave, then use The method of feeding hydrogen is used to get rid of the nitrogen in the autoclave;

[0033] Step 2. Heat the autoclave after nitrogen removal in step 1, and at the same time, continue to feed hydrogen into the autoclave, and make 3-hydroxypyridine catalyze in liquid phase under the conditions of temperature of 140°C and pressure of 4.0MPa Hydrogenation reduction reaction, after 13 hours of reaction, stop feeding hydrogen, filter and recover the ruthenium carbon catalyst after natural cooling, carry out vacuum distillation on the filtered filtrate at a temperature of 67°C-69°C...

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Abstract

The invention provides a method for preparing 3-hydroxypiperidine through liquid phase catalytic hydrogenation of 3-hydroxypyridine. The method includes the following steps: 1, adding the 3-hydroxypyridine, a ruthenium-carbon catalyst and pure water into a high-pressure reaction kettle, injecting nitrogen to discharge air in the kettle and injecting hydrogen to discharge the nitrogen in the kettle; 2, performing a liquid phase catalytic hydrogenation reduction reaction at the temperature of 140 DEG C under the pressure of 4.0MPa, filtering and recycling the ruthenium-carbon catalyst, performing reduced pressure distillation on filter liquor obtained after filtering, and collecting distillate to obtain the 3-hydroxypiperidine. The 3-hydroxypyridine serving as a raw material, ruthenium carbon serving as a catalyst and the pure water serving as a solvent are subjected to catalytic hydrogenation reduction to be composited into the 3-hydroxypiperidine, conversion rate reaches 100% and yield reaches above 95%; compared with a conventional reduction method in which rhodium carbon serves as the catalyst or methyl alcohol serves as the solvent, the method has the advantages of low cost, high yield and high quality.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for preparing 3-hydroxypiperidine by liquid-phase catalytic hydrogenation of 3-hydroxypyridine. Background technique [0002] 3-Hydroxypiperidine is an important intermediate for the synthesis of a chiral structure. Many piperidine derivatives have various pharmacological activities such as antibacterial, antitumor, treatment of Alzheimer's disease and anesthesia, and are also used for the treatment of viral infections (including AIDS) and one of the important drugs for diabetes. 3-hydroxypiperidine is mainly used in the synthesis of (S)-1-tert-butoxycarbonyl-3-hydroxypiperidine, etc., and has a wide range of uses and broad market prospects. In the existing synthesis production process, the raw materials are relatively expensive, and the process is long and complicated. The present invention uses the easily available 3-hydroxypyridine as the raw m...

Claims

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Application Information

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IPC IPC(8): C07D211/42
CPCC07D211/42Y02P20/584
Inventor 杨乔森张之翔文永忠黄琼淋樊小江唐良
Owner XIAN CATALYST NEW MATERIALS CO LTD
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