AT61181B - Process for the alkylation of morphine. - Google Patents
Process for the alkylation of morphine.Info
- Publication number
- AT61181B AT61181B AT61181DA AT61181B AT 61181 B AT61181 B AT 61181B AT 61181D A AT61181D A AT 61181DA AT 61181 B AT61181 B AT 61181B
- Authority
- AT
- Austria
- Prior art keywords
- morphine
- alkylation
- quaternary
- parts
- desc
- Prior art date
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Alkyllerung von Morphin.
Es wurde gefunden, dass man Morphin in guter Ausbeute in Kodein und seine Homologen in der Weise überführen kann, dass man dasselbe mit quaternären Ammoniumbasen, wie Phenyltriäthylammoniumhydroxyd oder Mischungen von Substanzen, die quaternäre Ammoniumbasen zu bilden vormögen, wie Phenyltrimethylammoniumchlorid oder Phenyl-1 trimothylammoniumjodid und alkoholische Kalilauge, behandelt.
Von den bisher bekannten Alkylierungsmethoden des Morphins unterscheidet sich diese Art der Alkylierung vorteilhaft dadurch, dass die Bildung der sonst als Nebenprodukte entstehenden quaternären Alkaloidsalze vermieden wird. Vor der Benutzung des
EMI1.1
besser durchführen lasst und die Reagenzien weniger giftig sind.
Die Reaktion verläuft in der Weise, dass die quaternäre Base in tertiäres Amin übergeht und der abgespaltene Alkohol in statu nascendi das Morphin in sone Äther überführt.
EMI1.2
Ausbeute an hoden nahezu theoretisch. Quaternäre Salze des Morphins oder Modems waren in nachweisbaren Mengen nicht vorhanden.
Beispiel 2 : 263 Teile Phenyltnmethylammoniuuljodid werden in absolutem Alkohol gelost und mit einer Lösung von 36 Teilen Ätzkali in absoluten Alkohol versetzt.
Das Gemisch wird mit 303 Teilen Morphin wie in Beispiel 1 behandelt.
In ähnlicher Weise lassen sich auch die Homologen des Kodeins darstellen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the alkylation of morphine.
It has been found that morphine can be converted into codeine and its homologues in good yield by converting the same with quaternary ammonium bases, such as phenyltriethylammonium hydroxide, or mixtures of substances which may form quaternary ammonium bases, such as phenyltrimethylammonium chloride or phenyl-1-methylammonium and iodide alcoholic potassium hydroxide solution.
This type of alkylation differs from the previously known alkylation methods of morphine in that it avoids the formation of the quaternary alkaloid salts which otherwise arise as by-products. Before using the
EMI1.1
perform better and the reagents are less toxic.
The reaction proceeds in such a way that the quaternary base changes into tertiary amine and the split-off alcohol converts the morphine into its ether in statu nascendi.
EMI1.2
The yield of testes is almost theoretical. Quaternary salts of morphine or modem were not present in detectable amounts.
Example 2: 263 parts of phenyltnmethylammonium iodide are dissolved in absolute alcohol and a solution of 36 parts of caustic potash in absolute alcohol is added.
The mixture is treated as in Example 1 with 303 parts of morphine.
The codeine homologues can also be represented in a similar manner.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT61181T | 1911-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT61181B true AT61181B (en) | 1913-09-10 |
Family
ID=3583037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT61181D AT61181B (en) | 1911-12-21 | 1911-12-21 | Process for the alkylation of morphine. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT61181B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1017618B (en) * | 1953-10-15 | 1957-10-17 | Dausse Sa Lab | Process for the preparation of the morpholylaethyl ether of morphine and its salts |
-
1911
- 1911-12-21 AT AT61181D patent/AT61181B/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1017618B (en) * | 1953-10-15 | 1957-10-17 | Dausse Sa Lab | Process for the preparation of the morpholylaethyl ether of morphine and its salts |
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