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
Application number
Other languages
German (de)
Inventor
Faust Edwin Stanton Dr Prof
Original Assignee
Faust Edwin Stanton Dr Prof
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Faust Edwin Stanton Dr Prof filed Critical Faust Edwin Stanton Dr Prof
Publication of CH93431A publication Critical patent/CH93431A/en

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)

PATENTANSPRÜCH: Verfahren zur Darstellung eines löslichen Derivates des Kampfers, dadurch gekenn zeichnet, dass man Metallsalze des Kampfer- säureimids mit ss-Halogen-äthyl-diäthylamin umsetzt. Das so erhaltene ss-Diäthylaminoäthyl- kampfersäureimid stellt ein dickflüssiges, unter 12 mm bei 183-185 siedendes Öl dar und bildet mit Säuren farblose, kristallinische, in Wasser und Alkohol lösliche, in Äther unlös liche Salze. Das Bromhydrat schmilzt bei 157 , das Chlorhydrat bei 89-90 . PATENT CLAIM: Process for the preparation of a soluble derivative of camphor, characterized in that metal salts of camphor imide are reacted with ß-halo-ethyl-diethylamine. The β-diethylaminoäthylkampersäureimid is a viscous oil boiling below 12 mm at 183-185 and forms colorless, crystalline salts which are soluble in water and alcohol and insoluble in ether. The bromine hydrate melts at 157, the chlorine hydrate at 89-90.
CH93431D 1919-10-15 1919-10-15 Process for the preparation of a soluble derivative of camphor. CH93431A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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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