CN101429129A - Method for extracting admantadine - Google Patents
Method for extracting admantadine Download PDFInfo
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- CN101429129A CN101429129A CNA2008102336134A CN200810233613A CN101429129A CN 101429129 A CN101429129 A CN 101429129A CN A2008102336134 A CNA2008102336134 A CN A2008102336134A CN 200810233613 A CN200810233613 A CN 200810233613A CN 101429129 A CN101429129 A CN 101429129A
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- amantadine
- water
- hydrochloric acid
- hydrochloride
- sodium hydroxide
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Abstract
The invention discloses a method for extracting amantadine, which aims to provide a method for extracting amantadine by a chemical means. The method has the advantages of simple technological process, little needed equipment and energy consumption, high yield, high purity of obtained amantadine and good quality. The invention adopts a technical proposal that after bromoadamantane and urea react to form water-insoluble amantadine, the amantadine is extracted according to the following steps: A. excessive hydrochloric acid is added to resultant, and the amantadine reacts with the hydrochloric acid to form water-soluble amantadine hydrochloride; and B. water-insoluble impurities are filtered and removed; excessive sodium hydroxide solution is added to residual solution; the amantadine hydrochloride and sodium hydroxide react to form the water-insoluble amantadine again; and the amantadine is filtered out. Due to the technical proposal of the invention, the amantadine yield of the method is higher than that of the prior process by more than 8 percent, and the purity of the obtained amantadine is more than 60 percent.
Description
Technical field
The present invention relates to a kind of extracting method of organic compound, in particular, relate to a kind of method of extracting amantadine.
Background technology
Amantadine is mainly used in makes a kind of antiviral---adamantanamine hydrochloride, it is a kind of intermediate product in this drug production process, adopt bromo diamantane and urea to produce as raw material, existing technical process of producing amantadine as shown in Figure 1, concrete production method is: after reactor is heated to 170 ℃, bromo diamantane and urea are added in the reactor, amination reaction takes place in the two, generate water-fast amantadine, its reaction formula is:
Bromo diamantane urea amantadine
Owing to contain water-fast impurity in the reactant, amantadine that generates and water-fast impurity bond together and make its purity drop, in order to remove these water-fast impurity, after reaction is finished amantadine is cooled to 100 ℃, with tap water amantadine and the water-fast impurity that bonds together is separated again; Add sodium hydroxide solution, heating makes temperature remain on 100 ℃-105 ℃, and sodium hydroxide, water and amantadine generation azeotropic distill amantadine and sodium hydroxide.There are several problems in the above-mentioned method of utilizing physics mode to extract amantadine: 1. the add-on of sodium hydroxide liquation is wayward, and add-on is little, and amantadine can not distill fully, and the yield of reaction is low, generally between 40%-50%; Add-on is big, can produce foam in the time of distillatory, and impurity sticks on the foam and distills together, and amantadine separates not thorough with impurity, and the amantadine purity that makes is low, and generally between 40%-50%, quality product is not high; 2. adopt the distillatory method that amantadine is purified, need use distillation plant, also will consume a large amount of energy, the production cost height.
Summary of the invention
The object of the present invention is to provide a kind of method of utilizing chemical means to extract amantadine, this method technological process is simple, and required equipment and consumes energy are few, the yield height, and the amantadine purity height that obtains, quality is good.
The present invention is achieved through the following technical solutions goal of the invention:
Bromo diamantane and urea reaction extract amantadine according to following steps after generating water-fast amantadine:
A, add excessive hydrochloric acid in resultant, following reaction takes place and generates water-soluble amantadine hydrochloride C in amantadine and hydrochloric acid
10H
17N.HCl, its reaction formula is as follows:
The amantadine amantadine hydrochloride
B, remove by filter water-fast impurity, in surplus solution, add excessive sodium hydroxide solution, amantadine hydrochloride C
10H
17N.HCl and sodium hydroxide react and generate water-fast amantadine once more, amantadine are filtered out get final product, and its reaction formula is as follows:
The amantadine hydrochloride amantadine
For amantadine and water-fast impurity separate easily are opened, after bromo diamantane and urea reaction generate amantadine, can produce thing cooling back and add tap water, amantadine and bond together, water-fast impurity separates.
The hydrochloric acid that adopts in the above-mentioned reaction is preferably concentrated hydrochloric acid.
Beneficial effect of the present invention is:
1. because the present invention has adopted the adding excessive hydrochloric acid, can fully the amantadine in the solution all be generated water-soluble C
10H
17N.HCl, adding excessive sodium hydroxide solution equally can be with C
10H
17N.HCl is converted to amantadine fully, so yield exceeds more than 8% than former technology.
2. the present invention has adopted the adding excessive hydrochloric acid, fully the amantadine in the solution is all generated water-soluble C
10H
17N.HCL can be clean water-fast contaminant filter, and the amantadine purity that obtains at last is greater than 60%, and quality product improves a lot.
3. the present invention has cancelled the distillatory step, directly adds chemical reagent and extracts diamantane, has reduced distillation plant, and the consumption of the energy greatly reduces production cost when also having reduced simultaneously distillation.
4. former process using adds sodium hydroxide and water and amantadine component distillation and extracts amantadine, sodium hydroxide adds the purity that too much can influence amantadine, cross that I haven't seen you for ages influences the yield of amantadine, the add-on of sodium hydroxide is wayward, and the employing technical solutions according to the invention can not only be extracted amantadine fully, and the amount ratio of each chemical reagent is easier to control, technological process is simple, and is easy to operate.
Description of drawings
Fig. 1 is for producing the process flow diagram of amantadine described in the background technology.
Embodiment
Adding 500Kg bromo diamantane and 180Kg urea make it to take place amination reaction in reactor, generation contains impurity, water-fast amantadine, treat that temperature reduces between 100 ℃-120 ℃, add the 950Kg tap water, fully stir, amantadine and the impurity that bonds together are separated, add concentrated hydrochloric acid again, up to solution PH=1, concentrated hydrochloric acid and amantadine react generate can be water-soluble the amantadine hydrochloride C10H17N.HCl aqueous solution, after the amantadine hydrochloride C10H17N.HCl aqueous solution removed by filter water-fast impurity, add sodium hydroxide solution in solution, up to solution PH=14, amantadine hydrochloride and sodium hydroxide react, generate water-fast amantadine once more, amantadine is filtered out get final product.
Claims (3)
1, a kind of extracting method of amantadine adopts bromo diamantane and urea reaction to generate water-fast amantadine, it is characterized in that, extracts amantadine according to following steps:
A, add excessive hydrochloric acid in resultant, following reaction takes place and generates water-soluble amantadine hydrochloride C in amantadine and hydrochloric acid
10H
17N.HCl, its reaction formula is as follows:
The amantadine amantadine hydrochloride
B, remove by filter water-fast impurity, in surplus solution, add excessive sodium hydroxide solution, amantadine hydrochloride C
10H
17N.HCl and sodium hydroxide react and generate water-fast amantadine once more, amantadine are filtered out get final product, and its reaction formula is as follows:
The amantadine hydrochloride amantadine
2, the extracting method of a kind of amantadine according to claim 1 is characterized in that, the hydrochloric acid of employing is concentrated hydrochloric acid.
3, the extracting method of a kind of amantadine according to claim 1 and 2, it is characterized in that, after bromo diamantane and urea reaction generate amantadine, to produce thing cooling back and add tap water, amantadine and bond together, water-fast impurity separates, and extracts amantadine according to two steps of A, B again.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008102336134A CN101429129A (en) | 2008-11-17 | 2008-11-17 | Method for extracting admantadine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008102336134A CN101429129A (en) | 2008-11-17 | 2008-11-17 | Method for extracting admantadine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101429129A true CN101429129A (en) | 2009-05-13 |
Family
ID=40644799
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008102336134A Pending CN101429129A (en) | 2008-11-17 | 2008-11-17 | Method for extracting admantadine |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107325005A (en) * | 2017-08-14 | 2017-11-07 | 四川众邦制药有限公司 | Separating and extracting process and device prepared by a kind of amantadine and its hydrochloride |
| CN109206320A (en) * | 2017-06-29 | 2019-01-15 | 江苏英力科技发展有限公司 | A kind of method of continuous production adamantanamine hydrochloride |
| CN111960949A (en) * | 2020-08-26 | 2020-11-20 | 中涛新材料有限公司 | High-yield amantadine preparation method |
| CN114409547A (en) * | 2022-01-27 | 2022-04-29 | 浙江普洛康裕制药有限公司 | Continuous production method and device of amantadine |
| CN115819248A (en) * | 2022-11-28 | 2023-03-21 | 四川化工职业技术学院 | Process for synthesizing amantadine hydrochloride based on continuous flow microreactor |
-
2008
- 2008-11-17 CN CNA2008102336134A patent/CN101429129A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109206320A (en) * | 2017-06-29 | 2019-01-15 | 江苏英力科技发展有限公司 | A kind of method of continuous production adamantanamine hydrochloride |
| CN107325005A (en) * | 2017-08-14 | 2017-11-07 | 四川众邦制药有限公司 | Separating and extracting process and device prepared by a kind of amantadine and its hydrochloride |
| CN111960949A (en) * | 2020-08-26 | 2020-11-20 | 中涛新材料有限公司 | High-yield amantadine preparation method |
| CN114409547A (en) * | 2022-01-27 | 2022-04-29 | 浙江普洛康裕制药有限公司 | Continuous production method and device of amantadine |
| CN115819248A (en) * | 2022-11-28 | 2023-03-21 | 四川化工职业技术学院 | Process for synthesizing amantadine hydrochloride based on continuous flow microreactor |
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Application publication date: 20090513 |