CH314216A - Process for the preparation of a quaternary ammonium salt - Google Patents

Process for the preparation of a quaternary ammonium salt

Info

Publication number
CH314216A
CH314216A CH314216DA CH314216A CH 314216 A CH314216 A CH 314216A CH 314216D A CH314216D A CH 314216DA CH 314216 A CH314216 A CH 314216A
Authority
CH
Switzerland
Prior art keywords
quaternary ammonium
ammonium salt
methyl
compound
methyl iodide
Prior art date
Application number
Other languages
German (de)
Inventor
E Speeter Merrill
Original Assignee
Bristol Lab Inc
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 Bristol Lab Inc filed Critical Bristol Lab Inc
Publication of CH314216A publication Critical patent/CH314216A/en

Links

Classifications

    • 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

  

  



  Verfahren zur Herstellung eines quaternären Ammoniumsalzes
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung eines neuen, von einem substituierten   Phenylaeetamid      abgelei-    teten quaternären Ammoniumsalzes, das dadurch gekennzeichnet ist, da.   eine Verbin-    dung der Formel
EMI1.1     
 mit. Methyljodid umgesetzt wird. Die so hergestellte Verbindung soll zu pharmazeutisehen   Zweeken    Verwendung finden.



   Die antispasmodische Wirkung des so erhaltenen quaternären Ammoniumsalzes ist der  jenigen    der freien   Base erheblieh iiberlegen.   



  Im weiteren kommt dem Salz auch eine   mydriatische Wirksamkeit    zu.



   Die als Ausgangsprodukt verwendete Base kann in bekannter Weise aus dem entspre  chenden    Nitril durch hydrolytisehe Umsetzung gewonnen werden.



   Beispiel
30 g a,   α-Diphenyl-ss-methyl-γ-diäthylamino-    butyronit. ril wurden mit 140 ml konzentrierter   Schwefelsäure und    14   ml    Wasser während 4 Stunden auf eine Innentemperatur von 95  C auf dem Wasserbad erhitzt. Das Reak  tionsgemiseh    wurde auf Eis gegossen und mit Ammoniumhydroxyd neutralisiert.

   Das sich ausscheidende Öl wurde aus Äthylacetat kristallisiert und zweimal aus Isopropanol umkristallisiert.,
8 g,   αα-Diphenyl-ss-methyl-γ-diäthylamino-      butyramid    (Smp.   135-137     C) wurden in 150 ml Äthanol in einer   Druekilasche    gelöst, 10 g Methyljodid zugegeben und die Mischung während 3 Stunden auf dem Wasserbad   er-    wärmt. Die Kristalle, die sieh beim   Abkuhlen    bilden, wurden dreimal aus Methanol um  krist. allisiert.   



   Das sich bildende quaternäre Jodid zeigte einen Smp. von   197-200     C.  



   PATENTANSPRUCH    Verfahren zur Herstellung eines quater- nären Ammoniumsalzes, dadurch gekennzeich-    net, dass eine Verbindung der Formel
EMI1.2     
 mit Methyljodid umgesetzt wird. 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.





  



  Process for the preparation of a quaternary ammonium salt
The present invention relates to a process for the production of a new quaternary ammonium salt derived from a substituted phenylaetamide, which is characterized in that. a compound of the formula
EMI1.1
 With. Methyl iodide is implemented. The compound thus produced is intended to be used for pharmaceutical purposes.



   The antispasmodic effect of the quaternary ammonium salt obtained in this way is considerably superior to that of the free base.



  The salt also has a mydriatic effect.



   The base used as the starting material can be obtained in a known manner from the corresponding nitrile by hydrolytic reaction.



   example
30 g of α, α-diphenyl-β-methyl-γ-diethylamino-butyronite. ril were heated with 140 ml of concentrated sulfuric acid and 14 ml of water for 4 hours to an internal temperature of 95 C on the water bath. The reaction mixture was poured onto ice and neutralized with ammonium hydroxide.

   The oil which separated out was crystallized from ethyl acetate and recrystallized twice from isopropanol.,
8 g of α-diphenyl-ss-methyl-γ-diethylamino-butyramide (melting point 135-137 C) were dissolved in 150 ml of ethanol in a pressure bottle, 10 g of methyl iodide were added and the mixture was left on for 3 hours Water bath warms up. The crystals that formed on cooling were crystallized three times from methanol. allized.



   The quaternary iodide that formed had a melting point of 197-200 C.



   PATENT CLAIM Process for the production of a quaternary ammonium salt, characterized in that a compound of the formula
EMI1.2
 is reacted with methyl iodide.

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. Verfahren zur Herstellung eines quaternären Ammoniumsalzes Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung eines neuen, von einem substituierten Phenylaeetamid abgelei- teten quaternären Ammoniumsalzes, das dadurch gekennzeichnet ist, da. eine Verbin- dung der Formel EMI1.1 mit. Methyljodid umgesetzt wird. Die so hergestellte Verbindung soll zu pharmazeutisehen Zweeken Verwendung finden. Process for the preparation of a quaternary ammonium salt The present invention relates to a process for the production of a new quaternary ammonium salt derived from a substituted phenylaetamide, which is characterized in that. a compound of the formula EMI1.1 With. Methyl iodide is implemented. The compound thus produced is intended to be used for pharmaceutical purposes. Die antispasmodische Wirkung des so erhaltenen quaternären Ammoniumsalzes ist der jenigen der freien Base erheblieh iiberlegen. The antispasmodic effect of the quaternary ammonium salt obtained in this way is considerably superior to that of the free base. Im weiteren kommt dem Salz auch eine mydriatische Wirksamkeit zu. The salt also has a mydriatic effect. Die als Ausgangsprodukt verwendete Base kann in bekannter Weise aus dem entspre chenden Nitril durch hydrolytisehe Umsetzung gewonnen werden. The base used as the starting material can be obtained in a known manner from the corresponding nitrile by hydrolytic reaction. Beispiel 30 g a, α-Diphenyl-ss-methyl-γ-diäthylamino- butyronit. ril wurden mit 140 ml konzentrierter Schwefelsäure und 14 ml Wasser während 4 Stunden auf eine Innentemperatur von 95 C auf dem Wasserbad erhitzt. Das Reak tionsgemiseh wurde auf Eis gegossen und mit Ammoniumhydroxyd neutralisiert. example 30 g of α, α-diphenyl-β-methyl-γ-diethylamino-butyronite. ril were heated with 140 ml of concentrated sulfuric acid and 14 ml of water for 4 hours to an internal temperature of 95 C on the water bath. The reaction mixture was poured onto ice and neutralized with ammonium hydroxide. Das sich ausscheidende Öl wurde aus Äthylacetat kristallisiert und zweimal aus Isopropanol umkristallisiert., 8 g, αα-Diphenyl-ss-methyl-γ-diäthylamino- butyramid (Smp. 135-137 C) wurden in 150 ml Äthanol in einer Druekilasche gelöst, 10 g Methyljodid zugegeben und die Mischung während 3 Stunden auf dem Wasserbad er- wärmt. Die Kristalle, die sieh beim Abkuhlen bilden, wurden dreimal aus Methanol um krist. allisiert. The oil which separated out was crystallized from ethyl acetate and recrystallized twice from isopropanol., 8 g of α-diphenyl-ss-methyl-γ-diethylamino-butyramide (melting point 135-137 C) were dissolved in 150 ml of ethanol in a pressure bottle, 10 g of methyl iodide were added and the mixture was left on for 3 hours Water bath warms up. The crystals that formed on cooling were crystallized three times from methanol. allized. Das sich bildende quaternäre Jodid zeigte einen Smp. von 197-200 C. The quaternary iodide that formed had a melting point of 197-200 C. PATENTANSPRUCH Verfahren zur Herstellung eines quater- nären Ammoniumsalzes, dadurch gekennzeich- net, dass eine Verbindung der Formel EMI1.2 mit Methyljodid umgesetzt wird. PATENT CLAIM Process for the production of a quaternary ammonium salt, characterized in that a compound of the formula EMI1.2 is reacted with methyl iodide.
CH314216D 1949-11-07 1950-11-07 Process for the preparation of a quaternary ammonium salt CH314216A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US314216XA 1949-11-07 1949-11-07
CH307790T 1950-11-07

Publications (1)

Publication Number Publication Date
CH314216A true CH314216A (en) 1956-05-31

Family

ID=25735325

Family Applications (1)

Application Number Title Priority Date Filing Date
CH314216D CH314216A (en) 1949-11-07 1950-11-07 Process for the preparation of a quaternary ammonium salt

Country Status (1)

Country Link
CH (1) CH314216A (en)

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