PL417206A1 - Method for obtaining quinine by way of deprotonation of hydrogen chloride or quinine sulfate in acetonitrile - Google Patents
Method for obtaining quinine by way of deprotonation of hydrogen chloride or quinine sulfate in acetonitrileInfo
- Publication number
- PL417206A1 PL417206A1 PL417206A PL41720616A PL417206A1 PL 417206 A1 PL417206 A1 PL 417206A1 PL 417206 A PL417206 A PL 417206A PL 41720616 A PL41720616 A PL 41720616A PL 417206 A1 PL417206 A1 PL 417206A1
- Authority
- PL
- Poland
- Prior art keywords
- quinine
- deprotonation
- acetonitrile
- sulfate
- obtaining
- Prior art date
Links
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 title abstract 12
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 title abstract 8
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 title abstract 6
- 235000001258 Cinchona calisaya Nutrition 0.000 title abstract 4
- 239000001576 FEMA 2977 Substances 0.000 title abstract 4
- 230000005595 deprotonation Effects 0.000 title abstract 4
- 238000010537 deprotonation reaction Methods 0.000 title abstract 4
- 229960000948 quinine Drugs 0.000 title abstract 4
- 229960003110 quinine sulfate Drugs 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- AKYHKWQPZHDOBW-UHFFFAOYSA-N (5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol Chemical compound OS(O)(=O)=O.C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 AKYHKWQPZHDOBW-UHFFFAOYSA-N 0.000 title abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 title 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 title 1
- LBSFSRMTJJPTCW-DSXUQNDKSA-N (r)-[(2s,4s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)C=C)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LBSFSRMTJJPTCW-DSXUQNDKSA-N 0.000 abstract 4
- 239000001096 (4-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol hydrochloride Substances 0.000 abstract 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 2
- 239000000706 filtrate Substances 0.000 abstract 2
- 239000002244 precipitate Substances 0.000 abstract 2
- 229960001811 quinine hydrochloride Drugs 0.000 abstract 2
- 230000005526 G1 to G0 transition Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Przedmiotem zgłoszenia jest sposób otrzymywania chininy, wzór 1, na drodze deprotonacji chlorowodorku lub siarczanu(VI) chininy w acetonitrylu, mający zastosowanie w syntezie chiralnych faz stacjonarnych do kolumn chromatograficznych. Sposób otrzymywania chininy, wzór 1, na drodze deprotonacji chlorowodorku lub siarczanu(VI) chininy w acetonitrylu, polega na tym, że dwuwodny chlorowodorek chininy albo jednowodny siarczan(VI) chininy, albo bezwodny chlorowodorek chininy, albo bezwodny siarczan(VI) chininy rozpuszcza się w acetonitrylu i poddaje reakcji chemicznej w temperaturze 20°C i czasie co najmniej 20 minut, następnie odsącza się wytrącony osad, zatęża przesącz do objętości równej od 5% do 15% objętości początkowej, dalej przesącz chłodzi się do temperatury 5°C, po czym odsącza się kolejną porcję wytrąconego osadu, następnie stałą pozostałość deprotonacji rozdrabnia się, w dalszej kolejności otrzymaną chininę poddaje się procesowi oczyszczania, a następnie suszy w temperaturze 30 ÷ 50°C pod obniżonym ciśnieniem.The subject of the application is the method of obtaining quinine, formula 1, by deprotonation of quinine hydrochloride or sulfate in acetonitrile, applicable in the synthesis of chiral stationary phases for chromatographic columns. The method of obtaining quinine, formula 1, by deprotonation of quinine hydrochloride or sulfate (VI) in acetonitrile consists in the fact that quinine hydrochloride dihydrate or quinine sulfate monohydrate or anhydrous quinine hydrochloride or anhydrous quinine sulfate in acetonitrile and subjected to a chemical reaction at 20 ° C and for at least 20 minutes, then the precipitate is filtered off, the filtrate is concentrated to a volume of 5% to 15% of the initial volume, then the filtrate is cooled to 5 ° C, then another portion of the precipitate is filtered off, then the solid deprotonation residue is crushed, then the quinine obtained is subjected to a purification process, and then dried at a temperature of 30 ÷ 50 ° C under reduced pressure.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL417206A PL236141B1 (en) | 2016-05-13 | 2016-05-13 | Method for obtaining quinine by way of deprotonation of hydrogen chloride or quinine sulfate in acetonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL417206A PL236141B1 (en) | 2016-05-13 | 2016-05-13 | Method for obtaining quinine by way of deprotonation of hydrogen chloride or quinine sulfate in acetonitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL417206A1 true PL417206A1 (en) | 2017-11-20 |
| PL236141B1 PL236141B1 (en) | 2020-12-14 |
Family
ID=60324468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL417206A PL236141B1 (en) | 2016-05-13 | 2016-05-13 | Method for obtaining quinine by way of deprotonation of hydrogen chloride or quinine sulfate in acetonitrile |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL236141B1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL449774A1 (en) * | 2024-10-02 | 2026-04-07 | Politechnika Poznańska | Quaternary ammonium salts of natural origin with a cation derived from quinine and an anion derived from L-alanine, method of obtaining them and use as algicides |
| PL449776A1 (en) * | 2024-10-02 | 2026-04-07 | Politechnika Poznańska | Quaternary ammonium salt with 1-(2-hydroxyethyl)quinine cation, method of obtaining it and use as a plant growth stimulator |
| PL449775A1 (en) * | 2024-10-02 | 2026-04-07 | Politechnika Poznańska | Quaternary ammonium salts with a cation derived from quinine and an L-aspartate anion, method of obtaining them and use as algicides |
-
2016
- 2016-05-13 PL PL417206A patent/PL236141B1/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL449774A1 (en) * | 2024-10-02 | 2026-04-07 | Politechnika Poznańska | Quaternary ammonium salts of natural origin with a cation derived from quinine and an anion derived from L-alanine, method of obtaining them and use as algicides |
| PL449776A1 (en) * | 2024-10-02 | 2026-04-07 | Politechnika Poznańska | Quaternary ammonium salt with 1-(2-hydroxyethyl)quinine cation, method of obtaining it and use as a plant growth stimulator |
| PL449775A1 (en) * | 2024-10-02 | 2026-04-07 | Politechnika Poznańska | Quaternary ammonium salts with a cation derived from quinine and an L-aspartate anion, method of obtaining them and use as algicides |
Also Published As
| Publication number | Publication date |
|---|---|
| PL236141B1 (en) | 2020-12-14 |
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