CH93431A - Process for the preparation of a soluble derivative of camphor. - Google Patents
Process for the preparation of a soluble derivative of camphor.Info
- Publication number
- CH93431A CH93431A CH93431DA CH93431A CH 93431 A CH93431 A CH 93431A CH 93431D A CH93431D A CH 93431DA CH 93431 A CH93431 A CH 93431A
- Authority
- CH
- Switzerland
- Prior art keywords
- camphor
- preparation
- soluble
- soluble derivative
- alcohol
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/417—Saturated compounds containing a keto group being part of a ring polycyclic
- C07C49/423—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system
- C07C49/427—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
- C07C49/433—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing seven carbon atoms
- C07C49/437—Camphor; Fenchone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
verfahren zur Darstellungseines löslichen Derivates des Kampfer,. Der allgemeinen Verwendung des Kamp- fers in der ärztlichen Praxis, speziell zu In jektionszwecken steht der Unstand entgegen, dass derselbe in Wasser schwer löslich ist.
Die Bestrebungen, den Kampfer durch solche Verbindungen zu ersetzen, welche seine charakteristischen wertvollen therapeutischen Eigenschaften besitzen, dabei aber leicht wasserlöslich und zugleich hitzebeständig und daher subcutan und intravenös steril injizier bar sind, haben bisher nicht zum Ziele geführt.
Es wurde null gefunden, @dass man zu einem Derivat des Kampfers gelangen kann, welchem diese Eigenschaften zukommen, indem man Metallsalze des Kanpfersäureimids mit ss- Halogen-äthyl-diätlylanin umsetzt.
Das so erhaltene ss-Diätliylaminoäthyl- kampfersäureimid
EMI0001.0011
stellt ein dickflüssiges, unter 12 min bei 183-18V siedendes Ol dar und bildet mit Säuren farblose, kristallinische, in Wasser und Alkohol lösliche, in Äther unlösliche Salze. Das Broinhydrat schmilzt bei 157 , das Chlor hydrat bei 89-90 .
Beispiel: Zu einer Lösung von 4,6 Teilen Natriun in absolutem Alkohol werden 18,1 Teile Kampfersäureimid und 26,1 Teile ss-Brom- äthyldiäthy lamm -Bromhydrat zugesetzt. Es wird dann bis zur völligen Ausscheidung des Bromnatriuns unter Rückfluss gelocht. Das Reaktionsprodukt wird angesäuert und durch Destillation vom Alkohol befreit. Der Rück stand gibt nach dem Alkalischinachen die ge suchte ssase all Wier ab. Zwecks Reinigung derselben wird der Äther abgetrieben und das hinterbleibende Öl im Vakuum destilliert, wobei die Base zwischen 183-185 unter 12 mm fast restlos übergeht.
Das Bromhydrat wird erhalten, indem inan die getrocknete ätherische Lösung der Base mit alkoholischerri Bromwasserstoff versetzt. Dasselbe wird zweek- mä l;ig aus Essigester und Alkohol umkristal lisiert. In äleiclier Weise gewinnt inan nlit Hilfe alkoholischer Salzsäure das Chlorhydrat der Base.
process for the preparation of a soluble derivative of camphor. The general use of camphor in medical practice, especially for injection purposes, is opposed by the fact that it is sparingly soluble in water.
Efforts to replace camphor with compounds which have its characteristic valuable therapeutic properties, but are easily water-soluble and at the same time heat-resistant and therefore sterile injectable subcutaneously and intravenously, have not yet led to the goal.
It was found zero that a derivative of camphor can be obtained, which has these properties, by reacting metal salts of the canoperimide with s-haloethyl dietlylanine.
The thus obtained ß-dietliylaminoäthylkampersäureimid
EMI0001.0011
is a viscous oil that boils at 183-18V for less than 12 minutes and forms colorless, crystalline salts with acids that are soluble in water and alcohol and insoluble in ether. The broin hydrate melts at 157, the chlorine hydrate at 89-90.
Example: To a solution of 4.6 parts of sodium in absolute alcohol, 18.1 parts of camphor imide and 26.1 parts of ss-bromine äthyldiäthy lamb bromohydrate are added. It is then refluxed until the bromine sodium is completely eliminated. The reaction product is acidified and freed from alcohol by distillation. The residue gives off the sought-after ssase all Wier after the alkaline chinache. To purify the same, the ether is driven off and the remaining oil is distilled in vacuo, the base passing over almost completely between 183-185 under 12 mm.
The bromohydrate is obtained by adding alcoholic hydrogen bromide to the dried ethereal solution of the base. It is recrystallized in two ways from ethyl acetate and alcohol. The hydrochloride of the base is obtained in a similar manner with the aid of alcoholic hydrochloric acid.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH93431T | 1919-10-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH93431A true CH93431A (en) | 1922-03-01 |
Family
ID=4350971
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH93431D CH93431A (en) | 1919-10-15 | 1919-10-15 | Process for the preparation of a soluble derivative of camphor. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH93431A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1098001B (en) * | 1957-09-12 | 1961-01-26 | Knoll Ag | Process for the preparation of N- (Diaethylaminoalkyl) -salicylamiden |
-
1919
- 1919-10-15 CH CH93431D patent/CH93431A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1098001B (en) * | 1957-09-12 | 1961-01-26 | Knoll Ag | Process for the preparation of N- (Diaethylaminoalkyl) -salicylamiden |
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