CH363658A - Process for the production of new scopin ethers - Google Patents
Process for the production of new scopin ethersInfo
- Publication number
- CH363658A CH363658A CH6333058A CH6333058A CH363658A CH 363658 A CH363658 A CH 363658A CH 6333058 A CH6333058 A CH 6333058A CH 6333058 A CH6333058 A CH 6333058A CH 363658 A CH363658 A CH 363658A
- Authority
- CH
- Switzerland
- Prior art keywords
- scopin
- ethers
- new
- production
- benzene
- Prior art date
Links
- FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 6
- -1 scopin ethers Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- FIMXSEMBHGTNKT-RZVDLVGDSA-N scopine Chemical compound C([C@@H]1N2C)[C@H](O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-RZVDLVGDSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FIMXSEMBHGTNKT-UPGAHCIJSA-N scopine Chemical compound C([C@@H]1N2C)C(O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-UPGAHCIJSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OQROAIRCEOBYJA-UHFFFAOYSA-N bromodiphenylmethane Chemical compound C=1C=CC=CC=1C(Br)C1=CC=CC=C1 OQROAIRCEOBYJA-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PVQATPQSBYNMGE-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PVQATPQSBYNMGE-UHFFFAOYSA-N 0.000 description 1
- JTBRUCSFYHKRFB-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 JTBRUCSFYHKRFB-UHFFFAOYSA-N 0.000 description 1
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical class C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000011230 binding agent Substances 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
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von neuen Scopinäthern Es wurde gefunden, dass man zu neuen Scopinäthern der Formel I
EMI0001.0004
gelangen kann, indem man Scopin mit einem Di- phenylmethan-Derivat der allgemeinen Formel II
EMI0001.0009
worin Hal für Chlor oder Brom steht, umsetzt.
Im Hauptpatent wird ein Verfahren zur Her stellung von Scopinäthern der Formel I beschrieben, wonach man Scopin mit einem Diphenyldiazomethan- Derivat der Formel III
EMI0001.0016
umsetzt. Es wurde nun gefunden, dass man auch zu Scopinäthern der Formel I gelangen kann, wenn man Scopin mit Diphenylhalogen-methan-Derivaten der Formel II veräthert.
Das Verfahren wird beispielsweise folgender massen ausgeführt: Scopin wird in Gegenwart eines halogenwasserstoffbindenden Mittels, wie beispiels weise Natriumäthylat oder Natriumcarbonat, bei er höhter Temperatur innerhalb von 1-2 Std. mit Di- phenylbrom-methan versetzt. Zur Vervollständigung der Reaktion wird die Lösung von 2-4 Std. bei 100-150 gehalten und anschliessend das ge wünschte Endprodukt nach bekannten Methoden iso liert.
<I>Beispiel</I> Scopinbenzhydryläther (6,7ss-Epoxy-tropih-3a-benz- hydryläther) Zu einer Mischung von 0,6 g Scopin und 0,3 g Natriumcarbonat lässt man bei 110 unter Rühren innert 11/2 Stunden eine Lösung von 0,96g Diphenyl- brommethan in 3 cm3 abs. Benzol zutropfen. An schliessend wird das Reaktionsgemisch noch 3 Stun den unter weiterem Rühren auf 125 gehalten.
Nach Abkühlen versetzt man mit 50 cm3 Wasser und 50 cm3 Benzol, schüttelt durch, trennt die Benzol schicht ab, und extrahiert den wässrigen Anteil por- tionenweise mit weiteren 200 cm3 Benzol. Die ver einigten Benzolauszüge werden sodann mit total 250 cm3 eisgekühlter, wässriger 2n-Salzsäure extra hiert.
Der salzsaure, wässrige Extrakt wird mit 50 cm? Äther gewaschen und unter starkem Kühlen mit wäss- riger 30proz. Natronlauge alkalisch gestellt. Man schüttelt mit total 350 cm3 Benzol aus, trocknet die vereinigten Benzolauszüge über Magnesiumsulfat und dampft das Benzol im Vakuum ab. Aus dem Rück stand wird mit der berechneten Menge methanolischer Salzsäure das Hydrochlorid hergestellt.
Nach Um kristallisation aus Methanol/Äther schmilzt das Scopinbenzhydryläther-hydrochlorid bei 209-212 (Zers.).
Process for the preparation of new scopin ethers It has been found that new scopin ethers of the formula I
EMI0001.0004
can be achieved by scopine with a diphenylmethane derivative of the general formula II
EMI0001.0009
wherein Hal stands for chlorine or bromine.
In the main patent, a process for the manufacture of scopine ethers of the formula I is described, after which scopine with a diphenyldiazomethane derivative of the formula III
EMI0001.0016
implements. It has now been found that scopine ethers of the formula I can also be obtained if scopine is etherified with diphenylhalomethane derivatives of the formula II.
The process is carried out, for example, as follows: Scopin is mixed with diphenylbromomethane in the presence of a hydrogen halide-binding agent, such as sodium ethylate or sodium carbonate, at an elevated temperature within 1-2 hours. To complete the reaction, the solution is kept at 100-150 for 2-4 hours and then the desired end product is isolated by known methods.
<I> Example </I> Scopin benzhydryl ether (6,7ss-epoxy-tropih-3a-benzhydryl ether) A mixture of 0.6 g scopine and 0.3 g sodium carbonate is left at 110 with stirring within 11/2 hours a solution of 0.96g diphenylbromomethane in 3 cm3 abs. Add benzene dropwise. The reaction mixture is then kept at 125 for a further 3 hours with continued stirring.
After cooling, 50 cm3 of water and 50 cm3 of benzene are added, the mixture is shaken, the benzene layer is separated off and the aqueous portion is extracted in portions with a further 200 cm3 of benzene. The combined benzene extracts are then extracted with a total of 250 cm3 of ice-cold, aqueous 2N hydrochloric acid.
The hydrochloric acid, aqueous extract is 50 cm? Ether washed and with strong cooling with aqueous 30%. Sodium hydroxide solution made alkaline. It is extracted with a total of 350 cm3 of benzene, the combined benzene extracts are dried over magnesium sulphate and the benzene is evaporated off in vacuo. The hydrochloride is prepared from the residue with the calculated amount of methanolic hydrochloric acid.
After crystallization from methanol / ether, the scopin benzhydryl ether hydrochloride melts at 209-212 (decomp.).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6333058A CH363658A (en) | 1957-10-15 | 1958-08-27 | Process for the production of new scopin ethers |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH360067T | 1957-10-15 | ||
| CH6333058A CH363658A (en) | 1957-10-15 | 1958-08-27 | Process for the production of new scopin ethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH363658A true CH363658A (en) | 1962-08-15 |
Family
ID=25737249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6333058A CH363658A (en) | 1957-10-15 | 1958-08-27 | Process for the production of new scopin ethers |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH363658A (en) |
-
1958
- 1958-08-27 CH CH6333058A patent/CH363658A/en unknown
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