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Synthetic method of amantadine hydrochloride

A technology for the synthesis of amantadine hydrochloride, which is applied in the preparation of carboxylic acid amides, chemical instruments and methods, and the preparation of amino compounds, etc., can solve problems such as excessive consumption, unrecyclable concentrated sulfuric acid and nitric acid, and rapid rise in reaction temperature. Achieve the effects of solving environmental pollution problems, good industrial application potential, and reducing waste gas production

Inactive Publication Date: 2020-05-01
广东仁康达材料科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, although the price of urea is low, the dosage needs to be greatly excessive. During the amination reaction, the reaction temperature is high and the reaction will suddenly heat up, which has certain safety hazards. Organic waste such as cyanuric acid and cyanuric acid amide is difficult to recycle, and the cost of waste water and residue treatment is relatively high
[0013] If adopt the route 1-2 of literature report, 1-3, 1-4, this kind of reaction has used fuming sulfuric acid, concentrated nitric acid or both mixture as solvent and oxygenant, can produce a large amount of acid waste gas (NO X , SO 2 etc.), and concentrated sulfuric acid and nitric acid cannot be recycled
At the same time, this reaction needs to be diluted with a large amount of water in the post-treatment process, and the amount of waste water is serious, so its industrial application is limited.

Method used

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  • Synthetic method of amantadine hydrochloride
  • Synthetic method of amantadine hydrochloride
  • Synthetic method of amantadine hydrochloride

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[0038] In order to solve the above problems, the first aspect of the present invention provides a kind of synthetic method of amantadine hydrochloride, comprising the following steps:

[0039] 1) Add adamantane, solvent I and initiator into the reaction kettle, and feed oxidant gas, and react at 30-100°C for 1-3 hours;

[0040] 2), add nitrile compound in step 1), react for 1~10h, after the reaction finishes, reclaim solvent I, obtain the solid A that sinks at the bottom of the kettle;

[0041] 3), the solid A obtained in step 2) is beaten and washed with the first mass part of water, and filtered to obtain acetylamantadine;

[0042] 4), put the acetylamantadine obtained in step 3) in an autoclave, dissolve it with solvent II, then add an alkaline substance and the second mass part of water, raise the temperature to 100-200°C, and react for 5-10 hours. , reclaim solvent II, and obtain solid B that sinks at the bottom of the kettle;

[0043] 5), adding the first mass part of ...

Embodiment 1

[0116] Embodiment 1 provides a kind of synthetic method of amantadine hydrochloride, comprising the following steps:

[0117] 1) Add 20g of adamantane, 120mL of solvent I and 0.16g of initiator into the reaction kettle, and feed oxidant gas, and react at 50°C for 2.5h;

[0118] 2), add 6.63g nitrile compound in step 1), react for 4h, after the reaction is finished, recover the solvent I, and obtain the solid A which sinks at the bottom of the kettle;

[0119] 3), the solid A obtained in step 2) was beaten and washed with 50 mL of water, and filtered to obtain acetylamantadine;

[0120] 4), put the acetylamantadine obtained in step 3) in an autoclave, add 35mL of solvent II to dissolve, then add 10.5g of alkaline substance and 5mL of water, heat up to 145°C, react for 8h, and recover the solvent after the reaction Ⅱ, obtain the solid B that sinks at the bottom of the kettle;

[0121] 5), add 50mL water to beat and wash solid B, filter to obtain solid C;

[0122] 6) Dissolve ...

Embodiment 2

[0146] Embodiment 2 provides a kind of synthetic method of amantadine hydrochloride, comprising the following steps:

[0147] 1) Add 20g of adamantane, 66mL of solvent I and 0.02g of initiator into the reaction kettle, and pass oxidant gas into it, and react for 2.5h at 50°C;

[0148] 2), add 2g nitrile compound in step 1), react for 4h, after the reaction finishes, recycle solvent I, obtain the solid A that sinks at the bottom of the kettle;

[0149] 3), the solid A obtained in step 2) was beaten and washed with 20 mL of water, and filtered to obtain acetylamantadine;

[0150] 4), put the acetylamantadine obtained in step 3) in an autoclave, add 26mL of solvent II to dissolve, then add 4g of alkaline substance and 2mL of water, raise the temperature to 145°C, and react for 8h. After the reaction, recover solvent II , to obtain the solid B sinking at the bottom of the kettle;

[0151] 5), add 20mL water to beat and wash solid B, filter to obtain solid C;

[0152] 6) Dissolv...

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Abstract

The invention relates to organic synthesis, in particular to a synthetic method of amantadine hydrochloride. The technical route mainly adopted by the method is as follows: adamantane and acetonitrileare subjected to a Ritter reaction in an acid medium, and a pure amantadine hydrochloride product is obtained through hydrolysis and purification. Compared with the prior art, by adopting a special process and components, amantadine hydrochloride with high yield is prepared, can be used for preparing medicines, has the effects of treating and preventing viral infection, and has important clinicalvalue and market value; the mutual synergistic effect of various components is utilized, the amantadine hydrochloride synthesis process is effectively improved, the amantadine hydrochloride synthesisprocess is green and environmentally friendly, solvents can be recycled, waste gas is remarkably reduced, the problem of environmental pollution in the amantadine hydrochloride synthesis process of atraditional process is effectively solved, the wastewater amount is greatly smaller than that of a previous technical route, and the amantadine hydrochloride synthesis process has good industrial application potential.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing amantadine hydrochloride. Background technique [0002] Amantadine hydrochloride is a symmetrical tricyclic amine, which can inhibit the penetration of the virus into the host cell, affect the uncoating of the virus, inhibit its reproduction, and has the effect of treating and preventing viral infection. Amantadine hydrochloride has a narrow antiviral spectrum and is mainly used for the prevention of Asian influenza A. The drug has obvious curative effect on Parkinson's paralysis, has good effect on relieving tremor and stiffness, and has a fast onset of action and obvious effect 48 hours after taking the drug. In view of this, the research on the synthetic method of amantadine hydrochloride has been widely concerned. [0003] Regarding the synthetic method of amantadine hydrochloride, the synthetic routes reported in the literature that have...

Claims

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Application Information

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IPC IPC(8): C07C209/62C07C211/38
CPCC07C209/62C07C211/38C07C231/06C07C2603/74C07C233/06
Inventor 黄志健梁学文陈子涛
Owner 广东仁康达材料科技有限公司
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