AT234914B - Process for the preparation of the new 6-morphine mononicotinic acid ester - Google Patents
Process for the preparation of the new 6-morphine mononicotinic acid esterInfo
- Publication number
- AT234914B AT234914B AT248162A AT248162A AT234914B AT 234914 B AT234914 B AT 234914B AT 248162 A AT248162 A AT 248162A AT 248162 A AT248162 A AT 248162A AT 234914 B AT234914 B AT 234914B
- Authority
- AT
- Austria
- Prior art keywords
- morphine
- acid ester
- new
- preparation
- mononicotinic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 title description 6
- 239000002253 acid Substances 0.000 title description 4
- 229960005181 morphine Drugs 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 125000000627 niacin group Chemical group 0.000 claims description 2
- 229960003512 nicotinic acid Drugs 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 6-morpholine-mononicotinic acid ester Chemical class 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung des neuen
6-Morphin-Mononicotinsäureesters
EMI1.1
<Desc/Clms Page number 2>
von Morphin mitkristallisieren aus Methanol/Wasser schmilzt der Ester bei 234 - 2350C : er erweist sich als identisch mit der nach Beispiel 1 erhaltenen Verbindung.
Beispiel 3: 1,5 g 3,6-Morphin-bis-nicorinsäureesterbase werden in 30mlMethanolgelöstund diese Lösung unter Rückfluss 14 h gekocht. Hierauf wird die etwas gelb gefärbte methylalkoholische Löi sung mit dem gleichen Volumen Wasser versetzt, worauf nach einigem Stehen der 6-Morpholin-mononi- cotinsäureester in einer Menge von 0, 9 g auskristallisiert.Das Reaktionsprodukt ist beinahe schmelzpunkt- rein (232 - 233, 5 C) und wird durch eine weitere Kristallisation aus verdünntem Methanol völlig rein er- halten : die Substanz erwies sich identisch mit der nach den Beispielen 1 und 2 erhaltenen Verbindung.
PATENTANSPRÜCHE :
1. Verfahren zur Darstellung des neuen 6-Morphin-mononicotinsäureesters, dadurch gekennzeichnet, dass man aus dem 3, 6-Morphin-bis-nicotinsäureester oder seinen Salzen durch Hydrolyse in wässeriger bzw. schwachsaurer Lösung oder durch Erhitzen einer alkoholischen, vorzugsweise methylalkoholischen
Lösung des genannten Esters in Form der freien Base zum Sieden einen Nicotinsäurerest abspaltet.
<Desc / Clms Page number 1>
Procedure for representing the new
6-morphine mononicotinic acid ester
EMI1.1
<Desc / Clms Page number 2>
co-crystallize from morphine from methanol / water, the ester melts at 234-2350C: it proves to be identical to the compound obtained according to Example 1.
Example 3: 1.5 g of 3,6-morphine-bis-nicoric acid ester base are dissolved in 30 ml of methanol and this solution is boiled under reflux for 14 hours. The slightly yellow-colored methyl alcoholic solution is then treated with the same volume of water, whereupon the 6-morpholine-mononicotinic acid ester crystallizes out in an amount of 0.9 g after standing for a while. The reaction product is almost pure at the melting point (232-233, 5 C) and is obtained completely pure by further crystallization from dilute methanol: the substance was found to be identical to the compound obtained according to Examples 1 and 2.
PATENT CLAIMS:
1. A process for the preparation of the new 6-morphine-mononicotinic acid ester, characterized in that the 3, 6-morphine-bis-nicotinic acid ester or its salts are hydrolyzed in an aqueous or weakly acidic solution or by heating an alcoholic, preferably methyl alcoholic
Solution of said ester in the form of the free base splits off a nicotinic acid residue at boiling point.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT248162A AT234914B (en) | 1962-03-27 | 1962-03-27 | Process for the preparation of the new 6-morphine mononicotinic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT248162A AT234914B (en) | 1962-03-27 | 1962-03-27 | Process for the preparation of the new 6-morphine mononicotinic acid ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT234914B true AT234914B (en) | 1964-07-27 |
Family
ID=3535091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT248162A AT234914B (en) | 1962-03-27 | 1962-03-27 | Process for the preparation of the new 6-morphine mononicotinic acid ester |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT234914B (en) |
-
1962
- 1962-03-27 AT AT248162A patent/AT234914B/en active
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