CN1265391A - Preparation of levorotary Alpha-methylamino-phenylacetone and repeated usage of separating agent - Google Patents
Preparation of levorotary Alpha-methylamino-phenylacetone and repeated usage of separating agent Download PDFInfo
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- CN1265391A CN1265391A CN 00100412 CN00100412A CN1265391A CN 1265391 A CN1265391 A CN 1265391A CN 00100412 CN00100412 CN 00100412 CN 00100412 A CN00100412 A CN 00100412A CN 1265391 A CN1265391 A CN 1265391A
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- methylephedrone
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- water
- sulfonic acid
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Abstract
Levorotary camphor sulfonic acid is used in resolution of methylamino-phenylacetone and water is used as solvent to produce levorotary methylamino-phenylacetone salt directly, which is dissolved in water and mixed with equivalent ammonia water and organic solvent t obtain levorotary methylamino-phenylacetone. Sulfuric acid is added to the mother liqor to eliminate the inorganic salt ammonium sulfate and the mother liquor after resolution is mixed with equivalent mamonia water, heated to recemize and added with equivalent sulfuric acid to eliminate ammonium sulfate for reuse.
Description
The invention belongs to the preparation method of medicine intermediate, α-left-handed N-methylephedrone is the important intermediate of preparation medical material medicine α-left-handed methylamine phenylpropyl alcohol.
About the fractionation of racemize N-methylephedrone, adopt always and make resolving agent as dextrorotation Threaric acid, d-camphorsulfonic acid, use organic solvent as resolution solvent, as methyl alcohol, ethanol, propyl alcohol, butanols.As No. 639126 reports of German Patent, No. 768772 reports of English Patent.But use a large amount of organic solvents in process of production, production cost height, deficiency in economic performance.And resolving agent does not have effectively economic method to carry out the recirculation use.
The objective of the invention is to adopt l-camphor sulfonic acid to make the resolving agent of α-N-methylephedrone, can effectively split, obtain α-left-handed N-methylephedrone at the aqueous solution.Carry out the alkali neutralization with ammoniacal liquor.Can make the easy repeated use of resolving agent l-camphor sulfonic acid.
In order to achieve the above object, must prepare l-camphor sulfonic acid,, make d-camphorsulfonic acid through sulfonation reaction because only there is the dextrorotation natural camphor in nature.Past owing to there is not natural left-handed camphor, therefore can not the Direct Sulfonation reaction make l-camphor sulfonic acid, the report of l-camphor sulfonic acid resolution of alpha-N-methylephedrone also of no use in history.Modern with artificial synthetic DL camphor, through sulfonation reaction, make the DL camphorsulfonic acid, make resolving agent with the dextrorotation phenylglycine then, can obtain dextrorotation phenylglycine l-camphor sulfonic acid salt, alkali is free removes the dextrorotation phenylglycine through adding, and gained l-camphor sulfonic acid sodium salt obtains l-camphor sulfonic acid through ion-exchange.
The present invention is dissolved in the racemize N-methylephedrone in certain water gaging with the equivalent l-camphor sulfonic acid, heating for dissolving, and crystallisation by cooling obtains left-handed N-methylephedrone l-camphor sulfonic acid salt.Mother liquor adds the ammoniacal liquor of equivalent, and racemization is carried out in heating, and then adds the sulfuric acid or the hydrochloric acid of ammoniacal liquor equivalent, is concentrated to a certain degree, and cool to room temperature removes by filter inorganic salt and removes sulfate of ammoniac or ammonia chloride.Mother liquor further is cooled to zero degree, gets left-handed N-methylephedrone l-camphor sulfonic acid salt again, l-camphor sulfonic acid is simply reused.With the left-handed N-methylephedrone salt of the l-camphor sulfonic acid that obtains, soluble in water, add equivalent ammoniacal liquor, separate obtaining left-handed N-methylephedrone, mother liquor adds the sulfuric acid or the hydrochloric acid of ammoniacal liquor equivalent, and solution concentration arrives to a certain degree, cool to room temperature, remove by filter inorganic salt sulfate of ammoniac or ammonia chloride, mother liquor is a l-camphor sulfonic acid solution, can repeat simple use.
Prepare left-handed N-methylephedrone with method of the present invention,, make water as resolution solvent owing to adopt l-camphor sulfonic acid to make resolving agent, economical and practical, and resolving agent ammoniacal liquor salify, convenient repeated use, economically feasible.
Further specified the present invention in order to illustrate better below by embodiment.
Embodiment:
32.6g racemize N-methylephedrone and 46.4g l-camphor sulfonic acid are dissolved in the 95ml water, heating for dissolving, crystallisation by cooling splits out left-handed N-methylephedrone salt, and filtering separation gets 35.5g salt, resolution yield 90%.Specific rotatory power [α]=-34.2 °.This salt is dissolved in the 100ml water, adds concentration 10% ammoniacal liquor 31.5g.With the left-handed N-methylephedrone of methylbenzene extraction, pressure reducing and steaming toluene obtains the left-handed N-methylephedrone of 14.62g.In mother liquor, add concentration 20% sulfuric acid 22.05g concentrating under reduced pressure to moisture be 100% concentration, cool to room temperature removes by filter the inorganic salt sulfate of ammoniac, mother liquor is the l-camphor sulfonic acid aqueous solution, is used to recycle.
Above-mentioned crystallization is gone out mother liquor behind the left-handed N-methylephedrone, and adding concentration is 10% ammoniacal liquor 38.54g, is heated to the 20-40 degree, 12 hours time, adding concentration then is 20% sulfuric acid 26.9g, concentrating under reduced pressure to moisture be 120% concentration, be cooled to 35 degree, remove by filter the inorganic salt sulfate of ammoniac.Further be cooled to 0 degree, crystallization goes out left-handed N-methylephedrone l-camphor sulfonic acid salt.
Claims (3)
1, a kind of preparation method of left-handed α-N-methylephedrone, said α-N-methylephedrone is
As resolving agent, use water as solvent resolution of racemic N-methylephedrone with l-camphor sulfonic acid, heating for dissolving, crystallisation by cooling obtains left-handed N-methylephedrone salt.Gained salt is soluble in water, add the organic solvent immiscible with water (as toluene, chlorine walk back and forth, ether) in, add equivalent ammoniacal liquor to it, water layer is separated with organic layer, and the organic solvent pressure reducing and steaming obtains left-handed N-methylephedrone, aqueous solution pressure reducing and steaming gets l-camphor sulfonic acid ammonia salt.
2, according to claim 1, gained l-camphor sulfonic acid ammonia salt is soluble in water, adds equivalent sulfuric acid or hydrochloric acid.Be concentrated to a certain degree.Cool to room temperature, crystallization go out inorganic salt sulfate of ammoniac or ammonia chloride, remove by filter inorganic salt, and mother liquor is the left-handed camphor sulphur aqueous solution, is used to recycle.
3, according to claim 1, with splitting the ammoniacal liquor of the mother liquid obtained adding equivalent in back, be heated to the 20-50 degree, treat that racemization is finished after, add the sulfuric acid or the hydrochloric acid of ammoniacal liquor equivalent.Be concentrated to a certain degree, be cooled to the 20-50 degree, crystallization goes out inorganic salt, removes by filter inorganic salt, and mother liquor further is cooled to the 0-10 degree, and crystallization goes out left-handed N-methylephedrone l-camphor sulfonic acid salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 00100412 CN1265391A (en) | 2000-01-31 | 2000-01-31 | Preparation of levorotary Alpha-methylamino-phenylacetone and repeated usage of separating agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 00100412 CN1265391A (en) | 2000-01-31 | 2000-01-31 | Preparation of levorotary Alpha-methylamino-phenylacetone and repeated usage of separating agent |
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| Publication Number | Publication Date |
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| CN1265391A true CN1265391A (en) | 2000-09-06 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN 00100412 Pending CN1265391A (en) | 2000-01-31 | 2000-01-31 | Preparation of levorotary Alpha-methylamino-phenylacetone and repeated usage of separating agent |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005118524A1 (en) * | 2004-06-02 | 2005-12-15 | Shanghai Institute Of Pharmaceutical Industry | Process for preparing [(s)-(-)alpha-methylamino phenylacetone]2 (2r, 3r)-tartaric acid derivates |
| CN107522636A (en) * | 2017-08-30 | 2017-12-29 | 赤峰艾克制药科技股份有限公司 | A kind of method for reclaiming camphorsulfonic acid |
-
2000
- 2000-01-31 CN CN 00100412 patent/CN1265391A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005118524A1 (en) * | 2004-06-02 | 2005-12-15 | Shanghai Institute Of Pharmaceutical Industry | Process for preparing [(s)-(-)alpha-methylamino phenylacetone]2 (2r, 3r)-tartaric acid derivates |
| CN107522636A (en) * | 2017-08-30 | 2017-12-29 | 赤峰艾克制药科技股份有限公司 | A kind of method for reclaiming camphorsulfonic acid |
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| PB01 | Publication | ||
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| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |