CH243029A - Process for the preparation of an N-substituted imino-di-fatty acid amide. - Google Patents

Process for the preparation of an N-substituted imino-di-fatty acid amide.

Info

Publication number
CH243029A
CH243029A CH243029DA CH243029A CH 243029 A CH243029 A CH 243029A CH 243029D A CH243029D A CH 243029DA CH 243029 A CH243029 A CH 243029A
Authority
CH
Switzerland
Prior art keywords
diethylamide
preparation
fatty acid
acid amide
acid
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R Geigy
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 Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH243029A publication Critical patent/CH243029A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines     N-substituierten        Imino-di-fettsäureamides.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines     N-substi-          tuierten        Imino-di-fettsäureamides.    Das Ver  fahren ist     dadurch.        gekennzeichnet,    dass man  eine Verbindung der Formel  
EMI0001.0008     
         und    eine     Verbindung    der Formel  
EMI0001.0011     
    worin X und Y reaktionsfähige, bei der       Reaktion    mit Ausnahme einer in ihnen ent  haltenen  
EMI0001.0013     
    sich abspaltende Reste bedeuten,

   zum     N-(n-          Butyl)        -imino-essigsäure-a-buttersäure    -     bis-di-          äthylamid    umsetzt.    Die neue     Verbindung    soll als Arzneimit  tel Verwendung finden.  



  <I>Beispiel:</I>  42,8 Teile     a-(n-Butylamino)-buttersäure-          diäthylamid    (dargestellt aus     a-Brom-butter-          säure-diäthylamid    und     n-Butylamin)    werden  in 100 Teilen     Tetralin    gelöst     und    zum Sieden  erhitzt.

   Dazu tropft man bei 180  die Lösung  von 15 Teilen     Chloressigsäure-diäthylamid    in  50 Teilen     Tetralin    und kocht die Mischung  10 Stunden weiter unter     Rückfluss.    Nach  dem Erkalten wird das ausgeschiedene Chlor  hydrat des     a-(n-Butylamino)-buttersäure-di-          äthylamides    durch Filtration entfernt.

   Aus  der     Tetralinlösung        wird    das gebildete     N-(n-          Butyl)        -imino-essigsäure    -     a-buttersäure-bis-di-          äthylamid    durch     Ausschütteln        mit    Salzsäure  isoliert, aus der salzsauren Lösung durch  Sättigen mit     Kaliumhydroxyd    abgeschieden  und in     Xylol    aufgenommen. Nach dem       Trocknen    und     Abdestillieren    des     Xylols    wird  das Produkt im Hochvakuum destilliert.

   Es  ist ein fast farbloses, in     .Wasser    leicht lös-           liches    01 vom Siedepunkt 148 bis 151  unter  0,12 mm     Hg.    Mit organischen Lösungsmit  teln ist es     mischbar    und gibt mit Säuren lös  liche Salze.  



  Zur gleichen     Verbindung    gelangt man  durch Umsetzung von     n-Butylamino-essig-          säure-diäthylamid    mit     a-Brom-buttersäure-          diäthylamid.  



  Process for the preparation of an N-substituted imino-di-fatty acid amide. The present patent relates to a process for the preparation of an N-substituted imino-di-fatty acid amide. The process is thereby. characterized in that one is a compound of the formula
EMI0001.0008
         and a compound of the formula
EMI0001.0011
    wherein X and Y are reactive, with the exception of one contained in them in the reaction
EMI0001.0013
    separating residues mean

   to N- (n-butyl) -imino-acetic acid-a-butyric acid - bis-diethylamide. The new compound is to be used as a drug.



  <I> Example: </I> 42.8 parts of a- (n-butylamino) -butyric acid diethylamide (prepared from a-bromo-butyric acid diethylamide and n-butylamine) are dissolved in 100 parts of tetralin and brought to the boil heated.

   To this, the solution of 15 parts of chloroacetic acid diethylamide in 50 parts of tetralin is added dropwise at 180 and the mixture is refluxed for a further 10 hours. After cooling, the precipitated chlorine hydrate of a- (n-butylamino) butyric acid diethylamide is removed by filtration.

   The N- (n-butyl) -imino-acetic acid-a-butyric acid-bis-diethylamide formed is isolated from the tetralin solution by shaking with hydrochloric acid, separated from the hydrochloric acid solution by saturation with potassium hydroxide and taken up in xylene. After drying and distilling off the xylene, the product is distilled in a high vacuum.

   It is an almost colorless oil which is easily soluble in water and has a boiling point of 148 to 151 below 0.12 mm Hg. It is miscible with organic solvents and produces salts which are soluble with acids.



  The same compound is obtained by reacting n-butylamino-acetic acid diethylamide with a-bromo-butyric acid diethylamide.

Claims (1)

PATENTANSPRUGH: Verfahren zur Herstellung eines N-sub- stituierten Imino-di-fettsäureamides, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0002.0014 und eine Verbindung der Formel EMI0002.0015 worin Y und Y reaktionsfähige, bei der Reaktion mit Ausnahme einer in ihnen ent haltenen EMI0002.0017 sich abspaltende Reste bedeuten, zum N-(n Butyl)-imino-essigsäure-a-buttersäure-bis-di- äthylamid umsetzt. PATENT APPLICATION: Process for the preparation of an N-substituted imino-di-fatty acid amide, characterized in that a compound of the formula EMI0002.0014 and a compound of the formula EMI0002.0015 wherein Y and Y are reactive, with the exception of one contained in them in the reaction EMI0002.0017 residues which are split off mean that converts to N- (n-butyl) -imino-acetic acid-α-butyric acid-bis-diethylamide. Die neue Verbindung bildet ein fast farb loses, in Wasser leicht lösliches 01 vom Siede punkt 148 bis 151 unter einem Druck von 0,12 mm Hg. Mit organischen Lösungsmit teln ist es mischbar und gibt mit Säuren lös liche Salze. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man a-(n-Butyl- amino)-buttersäure-diäthylamid mit Halogen- essigsäure-diäthylamid umsetzt. 2. The new compound forms an almost colorless, easily soluble oil with a boiling point of 148 to 151 under a pressure of 0.12 mm Hg. It is miscible with organic solvents and produces salts which are soluble with acids. SUBClaims: 1. Process according to claim, characterized in that a- (n-butyl-amino) -butyric acid diethylamide is reacted with haloacetic acid diethylamide. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man n-Butyl- amino-essigsäure-diäthylamid mit a-Halogen- buttersäure-diäthylamid umsetzt. A method according to patent claim, characterized in that n-butylamino-acetic acid diethylamide is reacted with a-halobutyric acid diethylamide.
CH243029D 1943-05-13 1943-05-13 Process for the preparation of an N-substituted imino-di-fatty acid amide. CH243029A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH243029T 1943-05-13
CH236876T 1945-03-15

Publications (1)

Publication Number Publication Date
CH243029A true CH243029A (en) 1946-06-15

Family

ID=25728199

Family Applications (1)

Application Number Title Priority Date Filing Date
CH243029D CH243029A (en) 1943-05-13 1943-05-13 Process for the preparation of an N-substituted imino-di-fatty acid amide.

Country Status (1)

Country Link
CH (1) CH243029A (en)

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