CN1442405A - Method of preparing 3-amino propane sulfonic acid - Google Patents
Method of preparing 3-amino propane sulfonic acid Download PDFInfo
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- CN1442405A CN1442405A CN 03117646 CN03117646A CN1442405A CN 1442405 A CN1442405 A CN 1442405A CN 03117646 CN03117646 CN 03117646 CN 03117646 A CN03117646 A CN 03117646A CN 1442405 A CN1442405 A CN 1442405A
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- aminopropanesulfonic acid
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Abstract
A process for preparing 3-amino propanesulfonic acid features the open loop ammoniation reaction of 1,3-propane sulfolactone as raw material with ammonia. Its advantages are simple operation, low cost, and high output rate (more than 99%).
Description
Technical field
What the present invention relates to is a kind of method that is used to prepare the intermediate 3-aminopropanesulfonic acid that can be used as gaba receptor agonist.
Background technology
The 3-aminopropanesulfonic acid is a kind of medicine intermediate that is used to prepare gaba receptor agonist.To the synthetic method of this compound, except that in Annalen der chemie 565 Bend (22～35), introducing to some extent, still find no other preparation and put forth energy to report.The synthesis preparation method that the document is reported for feed ammonia in ethanol, makes it saturated, and cooling adds 1 down, 3-propane sultone, and being warming up to 32 ℃ again reacts, and promptly obtains said product.This method is owing to use ethanol to make solvent, and the product that generates in the reaction is sticking shape in ethanol, easily be mingled with unreacted raw material, and reaction is difficult for fully, and purification difficult, and the loss during the product recrystallization is bigger.Experimental result shows that the yield of this method is generally about 85%, and purity＜90%.Therefore, the product for preparing with this method is as handling without recrystallization purifying, can't obtain purity greater than 98% product.
Summary of the invention
According to above-mentioned situation, the present invention will provide a kind of method of the synthetic 3-of preparation aminopropanesulfonic acid newly, and its raw material is easy to get, easy and simple to handle, reaction can approaching quantitatively be finished, and makes the target product of generation be easy to separate and the content height, thereby can have the favorable industrial productive value.
The present invention is used to prepare the method for 3-aminopropanesulfonic acid, and with 1,3-propane sultone is a raw material, carries out the open loop amination reaction and makes with ammonia.Reaction process is shown below:
In the reaction process that adopts aforesaid method, the ammonia that uses in the said open loop amination reaction can adopt the mode of adding strong aqua commonly used, and its mole dosage generally can be raw material 1, the 2-10 of 3-propane sultone doubly ends when the generation of solid product stops; In addition, also can adopt in reaction solution and to feed modes such as ammonia ends when no longer absorbing and carry out.Wherein, when adopting the latter to feed the mode of ammonia in reaction solution, its operation both can also can be adopted under the condition of suitably pressurization and carry out for carrying out under normal pressure.As adopting pressurization to feed the mode of ammonia, a kind of reference mode that can be used as concrete enforcement is to pressurize to feed the operation of ammonia under gauge pressure is the condition of 0.1～0.3Mpa.
Experimental result shows, in the above-mentioned preparation method of the present invention, said this open loop amination reaction to be adopting 1, any in 4-dioxane or the tetrahydrofuran (THF), or with the two mixed solvent as reaction medium in the effect of carrying out for well.When adopting the reaction medium of latter's mixed solvent form, experimental result shows, generally makes 1, and it 1: 3～5: 1 was ideal comparatively in the scope that the two mixed volume ratio of 4-dioxane and tetrahydrofuran (THF) is controlled at.
With the solvent of above-mentioned form during as reaction medium, carry out for helping successful reaction, and take into account yield and two aspects of quality of target product, generally can adopt make said as reaction medium solvent and the weight consumption ratio of raw material be (1～10): 1 get final product, and wherein preferably proportional range is (5～8): 1.
Adopt the reaction that aforesaid method of the present invention carried out.General normal temperature or a little heat condition under can carry out smoothly and finish.For example, for guaranteeing the speed that reaction is carried out and the yield of product, the temperature of reaction that can be used as the embodiment reference is 10 ℃～70 ℃ a scope.More preferred temperature of reaction is to be controlled in 30～50 ℃ the scope.
By above-mentioned preparation method's process as can be seen, the reaction raw materials that preparation method of the present invention carried out is easy to get, the reaction conditions gentleness, and easy and simple to handle.Experimental result shows that the carrying out of this reaction is comparatively complete, and because the mother liquor behind the separated product can also continue to adopt mode such as logical ammonia to proceed reaction and arrive and react completely, and therefore the yield of this reaction almost can reach or near 100% of quantitative values.The target product that the reaction back is generated is lenticular, thereby not only separate easily, and experimental result shows that also even to directly not carrying out further purification process such as recrystallization by separating the product that obtains in the reaction system, its content also can reach more than 99%.Therefore, the comprehensive cost that employing the inventive method prepares the 3-aminopropanesulfonic acid is low, has positive effect and the value used in industrial production.
According to foregoing,,, can also make modification, replacement or the change of various ways not breaking away under the above-mentioned basic fundamental thought of the present invention prerequisite according to the ordinary skill knowledge and the customary means of this area.
The embodiment of form is described in further detail foregoing of the present invention again by the following examples.But this should be interpreted as that the scope of the above-mentioned theme of the present invention only limits to following example.All technology that realizes based on foregoing of the present invention all belong to scope of the present invention.
Description of drawings
Fig. 1 is the IR collection of illustrative plates of the inventive method product.
Embodiment
Embodiment 1:
10g 1 is being housed, in the reaction flask of 3-propane sultone, is adding 100ml 1, the 4-dioxane after the stirring and dissolving, slowly adds strong aqua 50ml, reaction solution heats up, and is controlled at reaction below 50 ℃ 4 hours, leaves standstill crystallization, filter, use absolute ethanol washing, after the drying, get white crystal shape product 11.3g, yield 99.2%, its content＞99% is detected in mp＞270 ℃.
IR (KBr compressing tablet) characteristic peak: 3044cm
-1(NH
2); 1263～1248cm
-1(wide); 1035cm
-1(SO
3H).The infrared spectrogram of product as shown in Figure 1.With the infrared standard diagram contrast and the comparison of this compound, the two is in full accord.
Embodiment 2:
In reaction flask, add 10g 1,3-propane sultone, adding tetrahydrofuran (THF) 100ml also stirs, normal pressure feeds ammonia under 30 ℃ of-40 ℃ of conditions, react 4 hours till no longer absorb, be cooled to 10 ℃, separate out white crystal shape product, filter, use absolute ethanol washing, get white solid thing 10.1g, yield 88.0%, mp＞270 ℃, content＞98%.
IR (KBr compressing tablet) characteristic peak: 3044cm
-1(NH
2); 1263～1248cm
-1(wide); 1035cm
-1(SO
3H).Infrared spectrogram and Fig. 1 of product are basic identical.
Embodiment 3:
The 10g 1 that in autoclave, packs into, 3-propane sultone and 1,4-dioxane 50ml feeds ammonias down in 30 ℃-40 ℃, and makes the still internal pressure reach 0.2-0.3Mpa, till no longer absorbing to the ammonia that feeds.The taking-up reactant filters, and use absolute ethanol washing, must white crystal shape product 11.4g, and yield 99.8%, mp＞270 ℃.
IR (KBr compressing tablet) characteristic peak: 3044cm
-1(NH
2); 1263～1248cm
-1(wide); 1035cm
-1(SO
3H).The infrared spectrogram of product is also with Fig. 1 unanimity.
Claims (10)
1. be used to prepare the method for 3-aminopropanesulfonic acid, it is characterized in that with 1,3-propane sultone is a raw material, carries out the open loop amination reaction and makes with ammonia.
2. the method that is used to prepare the 3-aminopropanesulfonic acid as claimed in claim 1, the ammonia that it is characterized in that using in the said reaction is for using strong aqua, and its mole dosage is a raw material 1, and 3-propane sultone 2-10 is doubly.
3. the method that is used to prepare the 3-aminopropanesulfonic acid as claimed in claim 1 is characterized in that the ammonia that uses in the said reaction ends when ammonia extremely no longer absorbs for feeding in reaction solution.
4. the method that is used to prepare the 3-aminopropanesulfonic acid as claimed in claim 3 is characterized in that saidly feeding being operating as of ammonia depress in adding of gauge pressure 0.1～0.3Mpa and to carry out in reaction solution.
5. the method that is used to prepare the 3-aminopropanesulfonic acid as claimed in claim 1 is characterized in that said open loop amination reaction 1, carries out at least a reaction medium in 4-dioxane or the tetrahydrofuran (THF).
6. the method that is used to prepare the 3-aminopropanesulfonic acid as claimed in claim 5, it is characterized in that said open loop amination reaction is 1, carry out in the blending agent of 4-dioxane and tetrahydrofuran (THF), the two blended volume ratio is 1, the 4-dioxane: tetrahydrofuran (THF)=1: 3～5: 1.
7. as the described method that is used to prepare the 3-aminopropanesulfonic acid of one of claim 1 to 6, the weight consumption ratio of said solvent and raw material is (1～10) when it is characterized in that reacting: 1.
8. the method that is used to prepare the 3-aminopropanesulfonic acid as claimed in claim 7, the weight consumption ratio of said solvent and raw material is (5～8) when it is characterized in that reacting: 1.
9. as the described method that is used to prepare the 3-aminopropanesulfonic acid of one of claim 1 to 6, said temperature of reaction is 10～70 ℃ when it is characterized in that reacting.
10. the method that is used to prepare the 3-aminopropanesulfonic acid as claimed in claim 9, said temperature of reaction is 30～50 ℃ when it is characterized in that reacting.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03117646 CN1200929C (en) | 2003-04-09 | 2003-04-09 | Method of preparing 3-amino propane sulfonic acid |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03117646 CN1200929C (en) | 2003-04-09 | 2003-04-09 | Method of preparing 3-amino propane sulfonic acid |
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| Publication Number | Publication Date |
|---|---|
| CN1442405A true CN1442405A (en) | 2003-09-17 |
| CN1200929C CN1200929C (en) | 2005-05-11 |
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| CN 03117646 Expired - Lifetime CN1200929C (en) | 2003-04-09 | 2003-04-09 | Method of preparing 3-amino propane sulfonic acid |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7253306B2 (en) * | 2003-06-23 | 2007-08-07 | Neurochem (International) Limited | Pharmaceutical drug candidates and methods for preparation thereof |
| CN101597196A (en) * | 2003-06-23 | 2009-12-09 | 贝卢斯健康(国际）有限公司 | Improved drug candidate and preparation method thereof |
| CN101362709B (en) * | 2008-07-31 | 2011-09-14 | 杭州福斯特药业有限公司 | 3-amino propanesulfonic acid preparation method |
| CN109020842A (en) * | 2018-06-01 | 2018-12-18 | 万华化学集团股份有限公司 | A kind of preparation method of taurine ammonia |
| CN112387308A (en) * | 2020-12-23 | 2021-02-23 | 福州大学 | Self-supporting solid acidic ionic liquid catalyst and preparation method thereof |
-
2003
- 2003-04-09 CN CN 03117646 patent/CN1200929C/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7253306B2 (en) * | 2003-06-23 | 2007-08-07 | Neurochem (International) Limited | Pharmaceutical drug candidates and methods for preparation thereof |
| CN101597196A (en) * | 2003-06-23 | 2009-12-09 | 贝卢斯健康(国际）有限公司 | Improved drug candidate and preparation method thereof |
| CN101362709B (en) * | 2008-07-31 | 2011-09-14 | 杭州福斯特药业有限公司 | 3-amino propanesulfonic acid preparation method |
| CN109020842A (en) * | 2018-06-01 | 2018-12-18 | 万华化学集团股份有限公司 | A kind of preparation method of taurine ammonia |
| CN109020842B (en) * | 2018-06-01 | 2021-05-14 | 万华化学集团股份有限公司 | Preparation method of taurine ammonia |
| CN112387308A (en) * | 2020-12-23 | 2021-02-23 | 福州大学 | Self-supporting solid acidic ionic liquid catalyst and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1200929C (en) | 2005-05-11 |
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Address after: South two ring road, Xindu District, Chengdu, Sichuan Patentee after: Sichuan Kelun Pharmaceutical Co.,Ltd. Address before: South two ring road, Xindu District, Chengdu, Sichuan Patentee before: Sichuan Kelun Large Pharmaceutical Factory Co.,Ltd. |
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