CH126677A - Process for the preparation of a new basic derivative of the camphor series. - Google Patents
Process for the preparation of a new basic derivative of the camphor series.Info
- Publication number
- CH126677A CH126677A CH126677DA CH126677A CH 126677 A CH126677 A CH 126677A CH 126677D A CH126677D A CH 126677DA CH 126677 A CH126677 A CH 126677A
- Authority
- CH
- Switzerland
- Prior art keywords
- camphor
- melting point
- preparation
- new basic
- new
- Prior art date
Links
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical class C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 229940075930 picrate Drugs 0.000 claims description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- 229960000846 camphor Drugs 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 β-camphor nitrile acid amide Chemical class 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000243 solution Substances 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
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/24—Camphidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfuhren zur Darstellung eines neuen basischen Derivates der Kampferreihe. Es wurde gefunden, dass man zu einem neuen basischen Derivat der Kampf erreihe gelangen kann, indem man ss-Kampfernitril- säureamid mit Alkalien behandelt.
Bei der Einwirkung von Alkalien auf ss-Kampfernitrilsäureamid tritt eine intra- molekul.are Umlagerung im Sinne folgender Formeln ein:
EMI0001.0011
das heisst, es bildet sich ein getoimid des Kampf ersäureimids.
Die Alkalibehan.dlung erfolgt zweckmässig in Gegenwart von Lösungsmitteln und in der Wärme. Als besonders vorteilhaft hat sieh die Verwendung von alkoholischen Al ha.lien erwiesen.
Die neue Base bildet sehr schöne, flächen- reiclie, durchsichtige Kristalle vom Schmelz punkt<B>238';</B> sie löst sich ziemlich leicht in kaltem Wasser, schwerem in Äther, leichter in Benzol und in Benzin, sehr leicht in Chloroform und in Alkohol. Sie liefert ein in Wasser sehr leicht lösliches, kristallini sches Chlorhydrat vom Schmelzpunkt 230' und ein in gelben Nadeln kristallisierendes Pikrat vom Schmelzpunkt<B>293'.</B>
Die neue Verbindung soll zu therapeu tischen Zwecken verwendet werden. Beispiel: 5 Geawichtsteile- ss-K_ampfernitrilsäure- amid (B. 33, 2962) werden in 20 Volum# teilen Alkohol gelöst und mit 5 Volum- teilen methylalkoholischem Kali (1: 2) ver setzt.
Nach zirka einstündigem Erwärmen auf dem Wasserbade wird die Mischung mit Wasser verdünnt, der Alkohol verdunstet, die wässerige Lösung angesäuert und zwecks Entfernung kleiner Mengen Kämpfersäure und Kampfe@rsäureimid ausgeäthert. Hierauf wird die saure wässerige Lösung mit Na tronlauge alkalisch gemacht und erschöpfend mit Chloroform extrahiert. Die nach dem Ab destillieren des Chloroforms zurückbleibende Base wird durch Umkristallisieren aus hei ssem Wasser gereinigt.
Zwecks Herstellung des Chlorhydrates wird die wässerige Lösung der Base bis zur schwach sauren Reaktion mit Salzsäure versetzt und auf dem Wasser bade eingedampft.
Procedure for the presentation of a new basic derivative of the camphor series. It has been found that a new basic derivative of the Kampfer series can be obtained by treating β-camphor nitrile acid amide with alkalis.
When alkalis act on ß-camphor nitrile acid amide, an intramolecular rearrangement occurs in the sense of the following formulas:
EMI0001.0011
that is, a getoimide of the combat acid imide is formed.
The alkali treatment is expediently carried out in the presence of solvents and in the heat. The use of alcoholic alcohols has proven to be particularly advantageous.
The new base forms very beautiful, flat, transparent crystals with a melting point <B> 238 '; </B> It dissolves fairly easily in cold water, heavier in ether, more easily in benzene and in gasoline, very easily in chloroform and in alcohol. It yields a crystalline hydrochloride which is very easily soluble in water and has a melting point of 230 'and a picrate which crystallizes in yellow needles and has a melting point of <B> 293'. </B>
The new compound is intended to be used for therapeutic purposes. Example: 5 parts by weight ss-K_ampfernitrilsäure- amid (B. 33, 2962) are dissolved in 20 parts by volume of alcohol and mixed with 5 parts by volume of methyl alcoholic potash (1: 2).
After about one hour of warming on the water bath, the mixture is diluted with water, the alcohol evaporated, the aqueous solution acidified and etherified to remove small amounts of combat acid and combat acid imide. The acidic aqueous solution is then made alkaline with sodium hydroxide solution and extracted exhaustively with chloroform. The base remaining after the chloroform has been distilled off is purified by recrystallization from hot water.
To prepare the chlorohydrate, hydrochloric acid is added to the aqueous solution of the base until it becomes weakly acidic and the mixture is evaporated on the water bath.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH126677T | 1927-04-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH126677A true CH126677A (en) | 1928-07-02 |
Family
ID=4385266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH126677D CH126677A (en) | 1927-04-17 | 1927-04-17 | Process for the preparation of a new basic derivative of the camphor series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH126677A (en) |
-
1927
- 1927-04-17 CH CH126677D patent/CH126677A/en unknown
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