CN104130139B - The preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium - Google Patents
The preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium Download PDFInfo
- Publication number
- CN104130139B CN104130139B CN201410327493.XA CN201410327493A CN104130139B CN 104130139 B CN104130139 B CN 104130139B CN 201410327493 A CN201410327493 A CN 201410327493A CN 104130139 B CN104130139 B CN 104130139B
- Authority
- CN
- China
- Prior art keywords
- dinitrophenoxy
- preparation
- ethyl ammonium
- choline derivative
- described step
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Abstract
The preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium.2,4-DNP and glycol dibromide are mixed in organic solvent by the preparation method the present invention that the invention discloses a kind of new choline derivative, obtain 2-(2,4-dinitrophenoxy) monobromethane; Then the 2-obtained (2,4-dinitrophenoxy) monobromethane and triethylamine are mixed in organic solvent, obtain solid, finally filter the solid obtained and carry out drying treatment, obtain product.Preparation method of the present invention has simple to operate, cheaper starting materials, simple process, the purity advantages of higher of product.
Description
Technical field
The invention belongs to chemical medicine intermediate field, particularly relate to a kind of preparation method of new choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium.
Background technology
2,4-DNP derivative has very important physiologically active, can accelerate the metabolism Sum decomposition of fat, and choline is then that a kind of information indispensable in organism transmits molecule.The avtive spot of 2,4-DNP and choline combines by the present invention, thus has prepared a kind of new choline derivative, chemistry bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium by name.Realization of the present invention, for the further activity research of this compounds lays good basis.The choline derivative provided is a kind of new compound, and its preparation method has simple to operate, cheaper starting materials, simple process, the purity advantages of higher of product.Combined by the avtive spot of 2,4-DNP and choline, prepare a kind of new choline derivative, so far, also the synthetic route of this compound is not reported.
Summary of the invention
The object of this invention is to provide a kind of new choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) preparation method of ethyl ammonium (1), this preparation method has simple to operate, cheaper starting materials, simple process, the advantage that the purity of product is high.
In order to solve the problems of the technologies described above, the present invention is solved by following technical proposals:
A kind of preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium, method is as follows:
Step a: be mixed in organic solvent by 2,4-DNP and glycol dibromide, obtains 2-(2,4-dinitrophenoxy) monobromethane;
Step b: be mixed in organic solvent by the 2-obtained in step a (2,4-dinitrophenoxy) monobromethane and triethylamine, obtain solid, above-mentioned reaction is carried out in encloses container;
Step c: carrying out drying treatment to filtering the solid obtained in step b, obtaining product.
As preferably, in described step a, the temperature of mixing is 0 DEG C to 100 DEG C.
As preferably, in described step a, the temperature of mixing most preferably is 80 DEG C.If temperature is too low, it is very slow that reaction is carried out; If temperature of reaction is too high, then color can become very dark, by product increases, and productive rate reduces.
As preferably, the organic solvent in described step a adopts any one in benzene, tetrahydrofuran (THF), acetone, methylene dichloride, DMF, toluene, ether.
As preferably, the organic solvent in described step a adopts DMF.This solvent good solubility can increase the speed of reaction, and Reaction time shorten is raised the efficiency.
As preferably, in described step b, the temperature of mixing is 0 DEG C to 60 DEG C.
As preferably, in described step b, the temperature of mixing most preferably is 50 DEG C.Temperature is too low, and it is very slow that reaction is carried out; At this temperature, the reflowing result of acetone is best.
As preferably, the organic solvent in described step b adopts any one in tetrahydrofuran (THF), acetone, methylene dichloride, DMF, toluene, ether.
As preferably, the organic solvent in described step b adopts acetone.Use acetone as solvent, side reaction is less, and solubleness is very little in acetone for the product of generation, and directly separate out in solid form, be separated easy, purity is also higher.
As preferably, first the solid with ethyl acetate be mixed to get in step b is repeatedly washed in described step c, then carry out drying treatment.The solid be mixed to get being carried out drying treatment again through repeatedly washing, by a small amount of raw material in product solid and organic impurity removing, the purity of product can be improved.
Obesity patient is more and more general in the world, but for most people, fat-reducing is a kind of very difficult thing, and slimming medicine kind is also very many, but major part all exists larger side effect.And 2,4-DNP derivative has very important physiologically active, the metabolism Sum decomposition of fat can be accelerated, can as a kind of potential slimming medicine, but solubleness is not in vivo fine, nor can well enter in cell.Choline is then that in organism, indispensable a kind of information transmits molecule, and the compound after their combinations of two, has the effect of good fat metabolism.
The present invention, owing to have employed above technical scheme, has significant technique effect:
The inventive method has simple to operate, cheaper starting materials, simple process, the purity advantages of higher of product.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail:
Embodiment 1
In 100mL single port bottle, by 1.84g2,2, 4-dinitrophenol is mixed in 60mLN, in dinethylformamide, then in reaction flask, slowly drips glycol dibromide (5mL).Temperature of reaction is slowly warming up to 80 DEG C, and react 4 hours at such a temperature, reaction system presents light yellow.After reaction terminates, 60mL water is added to reaction flask, then this mixed solution (3x60mL) is extracted with ethyl acetate, merge organic phase saturated sodium-chloride washing (5x20mL) obtained, anhydrous sodium sulfate drying organic phase, concentrated organic phase, by the residue that obtains through column chromatography for separation, obtain jonquilleous solid chemical compound (2) (2.3g, productive rate 80%).
Solid chemical compound obtained above (2) is placed in 100mL single port bottle, adds 50mL acetone, then disposablely add 5mL triethylamine.Temperature of reaction is slowly raised to 50 DEG C, keeps backflow 2 hours at such a temperature, separate out product gradually.After reaction terminates, temperature is cooled to room temperature, through filtering, the crude solid ethyl acetate washing obtained for several times, can obtain bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium (1), 1.89g, productive rate 76%, light yellow solid.
In a word, the foregoing is only preferred embodiment of the present invention, all equalizations done according to the present patent application the scope of the claims change and modify, and all should belong to the covering scope of patent of the present invention.
Claims (10)
1. the preparation method of choline derivative bromination triethyl-2-(2, a 4-dinitrophenoxy) ethyl ammonium, it is characterized in that, method is as follows:
Step a: be mixed in organic solvent by 2,4-DNP and glycol dibromide, obtains 2-(2,4-dinitrophenoxy) monobromethane;
Step b: be mixed in organic solvent by the 2-obtained in step a (2,4-dinitrophenoxy) monobromethane and triethylamine, obtain solid, above-mentioned reaction is carried out in encloses container;
Step c: carrying out drying treatment to filtering the solid obtained in step b, obtaining product.
2. the preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium according to claim 1, it is characterized in that: in described step a, the temperature of mixing is 0
oc to 100
oc.
3. the preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium according to claim 2, it is characterized in that: in described step a, the temperature of mixing is 80
oc.
4. choline derivative bromination triethyl-2-(2 according to claim 1,4-dinitrophenoxy) preparation method of ethyl ammonium, it is characterized in that: the organic solvent in described step a adopts any one in benzene, tetrahydrofuran (THF), acetone, methylene dichloride, DMF, toluene, ether.
5. the preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium according to claim 4, is characterized in that: the organic solvent in described step a adopts DMF.
6. the preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium according to claim 1, it is characterized in that: in described step b, the temperature of mixing is 0
oc to 60
oc.
7. the preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium according to claim 6, it is characterized in that: in described step b, the temperature of mixing is 50
oc.
8. choline derivative bromination triethyl-2-(2 according to claim 1,4-dinitrophenoxy) preparation method of ethyl ammonium, it is characterized in that: the organic solvent in described step b adopts any one in tetrahydrofuran (THF), acetone, methylene dichloride, DMF, toluene, ether.
9. the preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium according to claim 1, is characterized in that: the organic solvent in described step b adopts acetone.
10. choline derivative bromination triethyl-2-(2 according to claim 1,4-dinitrophenoxy) preparation method of ethyl ammonium, it is characterized in that: first the solid with ethyl acetate be mixed to get in step b is repeatedly washed in described step c, then carry out drying treatment.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410327493.XA CN104130139B (en) | 2014-07-10 | 2014-07-10 | The preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410327493.XA CN104130139B (en) | 2014-07-10 | 2014-07-10 | The preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104130139A CN104130139A (en) | 2014-11-05 |
| CN104130139B true CN104130139B (en) | 2016-02-17 |
Family
ID=51803039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410327493.XA Expired - Fee Related CN104130139B (en) | 2014-07-10 | 2014-07-10 | The preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104130139B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1310372A (en) * | 1969-04-22 | 1973-03-21 | Ciba Geigy Ag | Phenoxyethylammonium compounds a process for their manufacture and plant growth-regulating preparations containing them |
| CN1169141A (en) * | 1994-08-04 | 1997-12-31 | C&C新药研究所 | Novel amine derivative, process for producing same, and use thereof as antiarrhythmic |
-
2014
- 2014-07-10 CN CN201410327493.XA patent/CN104130139B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1310372A (en) * | 1969-04-22 | 1973-03-21 | Ciba Geigy Ag | Phenoxyethylammonium compounds a process for their manufacture and plant growth-regulating preparations containing them |
| CN1169141A (en) * | 1994-08-04 | 1997-12-31 | C&C新药研究所 | Novel amine derivative, process for producing same, and use thereof as antiarrhythmic |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104130139A (en) | 2014-11-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109651225B (en) | Preparation method of 1-methyl-3-morphinyl-4-arylmercapto maleimide compound | |
| CN105218621B (en) | Dehydroabietic acid benzimidazole Schiff base heterocyclic derivatives with anti-tumor activity and preparation method therefor and application thereof | |
| CN106432030A (en) | Preparation method of brivaracetam | |
| CN108675948A (en) | A kind of beta-hydroxy selenide compound and preparation method | |
| CN106365986A (en) | Compounds and preparation methods thereof, and uses of compounds in synthesis of brivaracetam | |
| CN102304163A (en) | Fluorous synthesis method of betamethasone | |
| CN107216298A (en) | A kind of preparation method of butylphenyl phthaleine | |
| CN108863878A (en) | A kind of beta-hydroxy selenide compound and preparation method | |
| CN103254265B (en) | Abiraterone acetate trifluoroacetate and its preparation method and application | |
| CN109053542A (en) | A kind of chemical synthesis process of the bromo- 5- hydroxyl 1-isoindolinone of 6- | |
| CN104130139B (en) | The preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium | |
| CN104829515A (en) | Pregabalin impurity preparation method | |
| CN106588753B (en) | Pimanerin preparation method | |
| CN107235943A (en) | A kind of preparation method of high purity butylene phthalide | |
| CN107540575B (en) | Preparation method of sitagliptin intermediate | |
| CN108484518B (en) | 2- (2, 4, 6-trimethylphenylseleno) -5-methylbenzoxazole compound and preparation method thereof | |
| CN105152947A (en) | Preparation method of 2-amino-3,5-dibromobenzaldehyde | |
| CN104557934B (en) | A kind of synthetic method of sophocarpine | |
| WO2023071328A1 (en) | Method for synthesizing 8-amino-1-{[2-(trimethylsilyl)ethoxy]methoxy}octane-3-one | |
| CN108689892A (en) | 3- sulfonylations-indane ketone compounds and preparation method thereof | |
| CN102964233A (en) | Synthetic method of 3,5-2-fluoro-(trifluoromethyl)benzophenone | |
| CN111925310A (en) | 3-amino-4-arylseleno maleimide compound and preparation method thereof | |
| CN105481827A (en) | 2, 5-dichloro thiophene preparation method | |
| CN104387221A (en) | Synthesis method of peretinoin decarboxylative body impurities | |
| CN104817482A (en) | 2-substituted pyrrolidine compound, preparation method and application thereof in preparation of vildagliptin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160217 Termination date: 20180710 |