DE566035C - Process for the preparation of pure hydroiodides of alkaloids - Google Patents
Process for the preparation of pure hydroiodides of alkaloidsInfo
- Publication number
- DE566035C DE566035C DET39080D DET0039080D DE566035C DE 566035 C DE566035 C DE 566035C DE T39080 D DET39080 D DE T39080D DE T0039080 D DET0039080 D DE T0039080D DE 566035 C DE566035 C DE 566035C
- Authority
- DE
- Germany
- Prior art keywords
- alkaloids
- pure
- hydroiodides
- preparation
- quinine
- 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
Links
- 229930013930 alkaloid Natural products 0.000 title claims description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- IKIBSPLDJGAHPX-UHFFFAOYSA-N arsenic triiodide Chemical compound I[As](I)I IKIBSPLDJGAHPX-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 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 description 11
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 235000001258 Cinchona calisaya Nutrition 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- 229960000948 quinine Drugs 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 2
- 229940000488 arsenic acid Drugs 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- HJTAZXHBEBIQQX-UHFFFAOYSA-N 1,5-bis(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1CCl HJTAZXHBEBIQQX-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
Description
Verfahren zur Darstellung reiner Hydrojodide von Alkaloiden Das Hauptpatent betrifft die Herstellung reiner Hydrojodide von Alkaloiden dadurch, daß man die Alkaloide mit solchen Mengen von Arsentrijodid, die über den Bedarf an salzartig zu bindendem Jod nicht hinausgehen, in indifferenten Lösungsmitteln zusammenbringt, zweckmäßig bei gelinder Wärme. Beim Abkühlen der entsprechend konzentrierten Lösungen scheidet sich das reine Hydrojodid des Alkaloids aus, während Arsentrioxyd in Lösung zurückbleibt.Process for the preparation of pure hydroiodides of alkaloids The main patent relates to the production of pure hydroiodides of alkaloids by the fact that the Alkaloids with such amounts of arsenic triiodide that are salt-like over the need does not go beyond binding iodine, brings it together in inert solvents, useful with mild heat. When cooling the appropriately concentrated solutions the pure hydroiodide of the alkaloid separates out, while arsenic trioxide is in solution remains behind.
Es wurde nun gefunden, daß sich das Verfahren mit Vorteil auch unter Verwendung v on W asser oder den wässerigen Lösungen organischer Lösungsmittel durchführen läßt. Als organische Lösungsmittel kommen dabei in Betracht z. B. Methyl-, Äthyl- oder Propylalkohol, Aceton und andere. Beispielsweise verläuft die Umsetzung zwischen Chinin und Arsentrijodid glatt in io- bis gooi'oigem wässerigem Methylalkohol oder Äthylalkohol von gleichen Konzentrationen. -Ausführungsbeispiele t. i g Chinin und o,c9 g Arsentrijodi,d werden in io ccm io- bis 2o%igem Methylalkohol unter gelindem Erwärmen (5o bis 6o' C) gelöst. Das Chinindihydrojodid kristallisiert bei Zimmertemperatur.It has now been found that the process is also advantageous under Use w ater or the aqueous solutions of organic solvents leaves. As organic solvents come into consideration z. B. methyl, ethyl or propyl alcohol, acetone and others. For example, the implementation runs between Quinine and arsenic triiodide smoothly in io- to gooi'oigem aqueous methyl alcohol or Ethyl alcohol of equal concentrations. -Examples t. i g quinine and o, c9 g of arsenic triiodi, d are dissolved in 10 ccm of io- to 20% methyl alcohol under mild Warming (5o to 6o'C) dissolved. The quinine dihydroiodide crystallizes at room temperature.
2. Es wird wie nach Beispiel i verfahren, jedoch 3o- bis 6ooloiger Methylalkohol verwandt. Die Kristallisation des Chinindihydrojodids erfolgt bei o'.2. The procedure is as in Example i, but 3o to 6o Related to methyl alcohol. The crystallization of the quinine dihydroiodide takes place at O'.
Bei Wahl einer höheren Konzentration des Methylalkohols als 6o % scheidet sich mit der Konzentration zunehmend auch arsenige Säure ab, von der die Lösung des Hydrojodids abfiltriert und zur Kristallisation ge: bracht werden kann.If a higher concentration of methyl alcohol than 6o% is selected, it is different arsenic acid, from which the solution increases, also increases with the concentration the hydroiodide is filtered off and can be brought to crystallization.
Bei Verwendung von Äthylalkohol bzw. Aceton verläuft die Umsetzung in ähnlicher Weise. Zweckmäßig werden die Lösungsmittel so gewählt, daß gleichzeitig mit der Kristallisation des Mkaloidhydrojodids keine Abscheidung von arseniger Säure erfolgt.When using ethyl alcohol or acetone, the reaction takes place in a similar way. The solvents are expediently chosen so that at the same time with the crystallization of the mkaloid hydroiodide no separation of arsenic acid he follows.
Es ist bereits vorgeschlagen worden, Chinindihy drojodid durch Umsetzen von sauren Chininsalzen mit Kaliumjodid herzustellen. Bei Verwendung von Bisulfat versagt dieser Vorschlag vollkommen. Aber auch bei der Umsetzung des Dihydrochlorids mit Kaliumjodid entstehen stets teilweise ölige Abscheidungen von Chinindihydrojodid, die beim Erstarren unvermeidliche Einschlüsse aufnehmen, wodurch die Reinheit beeinträchtigt wird. Ganz abgesehen davon erhält man aber mit, dem vorliegenden Verfahren eine quantitative Ausbeute,- während -bei der Umsetzung mit Iialiumjodid sich bestenfalls eine Ausbeute von etwa 8o % erreichen läßt. Hierzu kommt, daß die vorliegende Arbeitsweise, auch wenn es sich um die Herstellung des Produkts in großem 114aßstabe handelt, betriebsmäßig keinerlei Schwierigkeiten bereitet.It has already been suggested that quinindihy drojodid by reacting of acidic quinine salts with potassium iodide. When using bisulfate this proposal fails completely. But also in the implementation of the dihydrochloride with potassium iodide there are always partially oily deposits of quinine dihydroiodide, which take up inevitable inclusions when solidifying, through which the purity is impaired. Quite apart from that, you get with, the present process a quantitative yield, - while -in the reaction with Iialiumiodid can at best achieve a yield of about 80%. For this comes that the present working method, even if it is about the production of the Product on a large scale, poses no operational difficulties.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET39080D DE566035C (en) | 1931-06-06 | 1931-06-06 | Process for the preparation of pure hydroiodides of alkaloids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET39080D DE566035C (en) | 1931-06-06 | 1931-06-06 | Process for the preparation of pure hydroiodides of alkaloids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE566035C true DE566035C (en) | 1932-12-09 |
Family
ID=7560383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET39080D Expired DE566035C (en) | 1931-06-06 | 1931-06-06 | Process for the preparation of pure hydroiodides of alkaloids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE566035C (en) |
-
1931
- 1931-06-06 DE DET39080D patent/DE566035C/en not_active Expired
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