CN104130139A - Preparation method of choline derivative, namely, bromotriethyl-2-(2,4-dinitrophenoxyl)ethylammonium - Google Patents
Preparation method of choline derivative, namely, bromotriethyl-2-(2,4-dinitrophenoxyl)ethylammonium Download PDFInfo
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- CN104130139A CN104130139A CN201410327493.XA CN201410327493A CN104130139A CN 104130139 A CN104130139 A CN 104130139A CN 201410327493 A CN201410327493 A CN 201410327493A CN 104130139 A CN104130139 A CN 104130139A
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Abstract
The invention discloses a preparation method of a choline derivative, namely, bromotriethyl-2-(2,4-dinitrophenoxyl)ethylammonium. The invention discloses a preparation method of a novel choline derivative. The preparation method comprises the following steps: mixing 2,4-dinitrophenol and 1,2-dibromoethane into an organic solvent to obtain 2-(2,4-dinitrophenoxyl)bromoethane; mixing the obtained 2-(2,4-dinitrophenoxyl)bromoethane and triethylamine into the organic solvent to obtain a solid; and drying the filtered solid to obtain a product. The preparation method disclosed by the invention has the advantages of easiness in operation, adoption of cheap raw materials, simple and convenient process, high product purity and the like.
Description
Technical field
The invention belongs to chemical medicine intermediate field, related in particular 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 fatty metabolism and decomposition, and choline is that a kind of information indispensable in organism is transmitted molecule.The present invention combines the avtive spot of 2,4-DNP and choline, thereby 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 is laid good basis.The choline derivative providing is a kind of new compound, and its preparation method has simple to operate, raw material cheapness, simple process, the purity advantages of higher of product.The avtive spot of 2,4-DNP and choline is combined, 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, raw material cheapness, simple process, the high advantage of purity of product.
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: 2,4-DNP and glycol dibromide are mixed in organic solvent, obtain 2-(2,4-dinitrophenoxy) monobromethane;
Step b: the 2-obtaining in step a (2,4-dinitrophenoxy) monobromethane and triethylamine are mixed in organic solvent, obtain solid, above-mentioned reaction is carried out in encloses container;
Step c: carry out drying treatment to filtering the solid obtaining in step b, obtain 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, can color become very dark, by product increases, and productive rate reduces.
As preferably, the organic solvent in described step a adopts any 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 backflow effect of acetone is best.
As preferably, the organic solvent in described step b adopts any in tetrahydrofuran (THF), acetone, methylene dichloride, DMF, toluene, ether.
As preferably, the organic solvent in described step b adopts acetone.Use acetone to make solvent, side reaction is less, and the product of generation solubleness in acetone is very little, directly separates out with solid form, separates easyly, and purity is also higher.
As preferably, in described step c, first the solid being mixed to get in step b is repeatedly washed by ethyl acetate, then carry out drying treatment.The solid being mixed to get, through repeatedly washing and carry out drying treatment again, can be removed a small amount of raw material and organic impurity in product solid, improved the purity of product.
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, can accelerate fatty metabolism and decomposition, can be used as a kind of potential slimming medicine, but solubleness in vivo not fine, nor can well enter in cell.Choline is that a kind of information indispensable in organism is transmitted molecule, and the compound after their combinations of two has the effect of good fat metabolism.
The present invention, owing to having adopted above technical scheme, has significant technique effect:
The inventive method has simple to operate, raw material cheapness, 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 60mL DMF, then in reaction flask, slowly drips glycol dibromide (5mL).Temperature of reaction is slowly warming up to 80 DEG C, reacts 4 hours at this temperature, reaction system presents light yellow.After reaction finishes, add 60mL water to reaction flask, then be extracted with ethyl acetate this mixed solution (3x60mL), merge the organic phase saturated sodium-chloride washing (5x20mL) obtaining, anhydrous sodium sulfate drying organic phase, concentrated organic phase, by the residue process column chromatography for separation obtaining, 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, follow the disposable 5mL of adding triethylamine.Temperature of reaction is slowly raised to 50 DEG C, at this temperature, keeps refluxing 2 hours, separate out gradually product.After reaction finishes, temperature is cooled to room temperature, through filtering, the crude product solid ethyl acetate washing obtaining 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 of doing 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 a choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium, is characterized in that, method is as follows:
Step a: 2,4-DNP and glycol dibromide are mixed in organic solvent, obtain 2-(2,4-dinitrophenoxy) monobromethane;
Step b: the 2-obtaining in step a (2,4-dinitrophenoxy) monobromethane and triethylamine are mixed in organic solvent, obtain solid, above-mentioned reaction is carried out in encloses container;
Step c: carry out drying treatment to filtering the solid obtaining in step b, obtain product.
2. the preparation method of choline derivative bromination triethyl-2-according to claim 1 (2,4-dinitrophenoxy) ethyl ammonium, 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-according to claim 2 (2,4-dinitrophenoxy) ethyl ammonium, 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 in benzene, tetrahydrofuran (THF), acetone, methylene dichloride, DMF, toluene, ether.
5. the preparation method of choline derivative bromination triethyl-2-according to claim 4 (2,4-dinitrophenoxy) ethyl ammonium, is characterized in that: the organic solvent in described step a adopts DMF.
6. the preparation method of choline derivative bromination triethyl-2-according to claim 1 (2,4-dinitrophenoxy) ethyl ammonium, 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-according to claim 6 (2,4-dinitrophenoxy) ethyl ammonium, 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 in tetrahydrofuran (THF), acetone, methylene dichloride, DMF, toluene, ether.
9. the preparation method of choline derivative bromination triethyl-2-according to claim 1 (2,4-dinitrophenoxy) ethyl ammonium, 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: in described step c, first the solid being mixed to get in step b ethyl acetate is repeatedly washed, then carry out drying treatment.
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| 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 |
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| CN201410327493.XA CN104130139B (en) | 2014-07-10 | 2014-07-10 | The preparation method of choline derivative bromination triethyl-2-(2,4-dinitrophenoxy) ethyl ammonium |
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| CN104130139A true CN104130139A (en) | 2014-11-05 |
| CN104130139B CN104130139B (en) | 2016-02-17 |
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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 |
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