Method for synthesizing piperidine and homolog thereof from N-pyridine oxide and homolog thereof

A technology for oxidizing pyridine and homologues, applied in organic chemistry and other directions, can solve the problems of large pollution, low yield, excessive energy consumption, etc., and achieve the effects of reducing energy consumption, high yield, and wide application prospects.

Inactive Publication Date: 2018-11-20
ANHUI COSTAR BIOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method will produce a large amount of acid radical anions, which will pollute the environment relatively; the cycloaddition method can synthesize a six-membered heterocycle with biological activity, but this method has obvious limitations in actual production and application because the yield is too low; The hydrogenation reduction method is to react pyridine under high temperature and high pressure conditions in a hydrogen atmosphere to obtain piperidine. This method has a high yield, but because the reducing agent is hydrogen, the risk of the reaction is increased, and the reaction is performed under high temperature and high pressure conditions, which consumes energy also too big
In order to solve the problem of large environmental pollution, low yield, high energy consumption such as high temperature and high pressure due to the production of acid radical anions in the synthesis process of piperidine and its homologues, and it is more dangerous

Method used

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Effect test

Embodiment 1

[0016] A method for synthesizing piperidine and its homologues with pyridine N-oxide and its homologues, comprising the steps of: first weighing 95 g of pyridine N-oxide, 63 g of formic acid, and 500 mL of methanol, then placing pyridine N-oxide and ammonium formate In the reaction kettle, methanol was added, the temperature was controlled at 30° C., and the reaction was evenly stirred for 14 hours. After the stirring was completed, water was added to wash, and finally the solvent was removed by vacuum distillation to obtain 68 g of the product piperidine, and the product yield was 95.7%.

Embodiment 2

[0018] A method for synthesizing piperidine and its homologues with pyridine N-oxide and its homologues, comprising the steps of: first weighing 95 g of pyridine N-oxide, 63 g of formic acid, and 500 mL of methanol, then placing pyridine N-oxide and ammonium formate Add methanol to the reaction kettle, control the temperature at 25°C and uniformly stir the reaction for 14 hours. After the stirring is completed, add water to wash, and finally remove the solvent by vacuum distillation to obtain 67.5 g of the product piperidine, and the product yield is 95.1%.

Embodiment 3

[0020] A method for synthesizing piperidine and its homologues with N-oxidized pyridine and its homologues, comprising the steps of: first weighing 109 g of N-oxidized-3-picoline, 63 g of formic acid, and 500 mL of methanol, and then N-oxidized -3-Methylpyridine and ammonium formate are placed in a reaction kettle, methanol is added, the temperature is controlled at 30°C and the reaction is uniformly stirred for 14 hours. After the stirring is completed, water is added for washing, and finally the solvent is removed by distillation under reduced pressure to obtain the product 3-methylpiperidine Pyridine 83g, the product yield was 97.6%.

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Abstract

The invention discloses a method for synthesizing piperidine and homolog thereof from N-pyridine oxide and homolog thereof. The method comprises the following steps: firstly weighing 95-110g of N-pyridine oxide and homolog thereof, 63g of formic acid and 500mL of a solvent, putting the N-pyridine oxide and homolog thereof and ammonium formate into a reaction kettle, adding the solvent, controllingthe temperature to 25-35 DEG C, uniformly stirring to carry out a reaction, washing with water after stirring is completed, and finally carrying out vacuum distillation to remove the solvent, therebyobtaining a product. By adopting the method disclosed by the invention, the problems that piperidine and homolog thereof are serious in environment pollution, low in yield, high in temperature and pressure, high in energy consumption and the like in a synthesis process since acid radical anion is generated can be solved, the method has the advantages of good environment protection, energy conservation, security and high yields, the yield of the product is up to 95% or greater, which is far greater than that of a conventional cycloaddition method, in addition, when reactions are carried out under normal temperature and normal pressure conditions, energy consumption in the reaction process can be reduced, the purposes of energy conservation and environment protection are achieved, and wideapplication prospects can be met.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a method for synthesizing piperidine and its homologues with N-oxidized pyridine and its homologues. Background technique [0002] The synthetic methods of piperidine and its homologs are generally divided into cyclization method, cycloaddition method and hydrogenation reduction method. According to the different properties of the bond, the cyclization method can be divided into two categories: (1) by forming a C-N bond to form The cyclization method of the ring; (2) the cyclization method of forming a ring by forming a C-C bond. However, this method will produce a large amount of acid radical anions, which will pollute the environment relatively; the cycloaddition method can synthesize a six-membered heterocycle with biological activity, but this method has obvious limitations in actual production and application because the yield is too low; The hydrogenatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/023C07D295/027C07D211/12
CPCC07D211/12C07D295/023C07D295/027
Inventor 孙健何睦军赵维达汪小华李裕红肖跃军
Owner ANHUI COSTAR BIOCHEM CO LTD
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