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
Application number
Other languages
German (de)
Inventor
Rupe Hans Dr Prof
Original Assignee
Rupe Hans 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 Rupe Hans Dr Prof filed Critical Rupe Hans Dr Prof
Publication of CH126677A publication Critical patent/CH126677A/en

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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

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)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen basischen Derivates der Kampferreihe von der Formel:. EMI0002.0003 dadurch gekennzeichnet, dass man ,B-Kampfer- nitrilsäureamid mit Alkalien behandelt. Die neue Base bildet sehr schöne, flächen reiche, durchsichtige Kristalle vom Schmelz punkt 238 ; sie löst sich ziemlich leicht in kaltem Wasser, schwer in Äther, leichter in Benzol und in Benzin, sehr leicht in Chloroform und in Alkohol. PATENT CLAIM: Process for the preparation of a new basic derivative of the camphor series of the formula :. EMI0002.0003 characterized in that, B-camphor nitrilic acid amide is treated with alkalis. The new base forms very beautiful, flat, transparent crystals with a melting point of 238; it dissolves fairly easily in cold water, difficult in ether, more easily in benzene and gasoline, very easily in chloroform and alcohol. 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. It provides a crystalline hydrochloride, which is very easily soluble in water, with a melting point of 230 'and a picrate with a melting point of <B> 293' which crystallizes in yellow needles. </B> The new compound is intended to be used for therapeutic purposes.
CH126677D 1927-04-17 1927-04-17 Process for the preparation of a new basic derivative of the camphor series. CH126677A (en)

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)

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