CH314215A - Process for the preparation of a quaternary ammonium salt - Google Patents

Process for the preparation of a quaternary ammonium salt

Info

Publication number
CH314215A
CH314215A CH314215DA CH314215A CH 314215 A CH314215 A CH 314215A CH 314215D A CH314215D A CH 314215DA CH 314215 A CH314215 A CH 314215A
Authority
CH
Switzerland
Prior art keywords
quaternary ammonium
ammonium salt
preparation
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 CH314215A publication Critical patent/CH314215A/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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  



  Verfahren zur Herstellung eines quaternären Ammoniumsalzes
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung eines neuen, von einem substituierten Phenylacetamid abgeleiteten quaternären Ammoniumsalzes, das dadurch gekennzeichnet ist, dass eine Verbin  dune der    Formel
EMI1.1     
 mit   Methyl jodid umgesetzt    wird. Die so hergestellte Verbindung soll zu pharmazeutischen   Zweeken Verwendung finden.   



   Die antispasmodisehe Wirkung des so erhal  tenen quaternären Ammoniumsalzes ist    der  jenigen    der freien Base erheblich  berlegen.



     Im.    weiteren kommt dem Salz auch eine mydriatische Wirksamkeit zu.



   Die als Ausgangsprodukt verwendete Base kann in bekannter Weise aus dem entspreehenden Nitril durch hydrolytische   Umset-zlmg    ewonnen werden.



   Beispiel
30 g   α,      a-Diphenyl-y-diäthylamino-valero-    nitril wurden mit 140 ml konzentrierter Sehwefelsäure und 14 ml Wasser während
Stunden auf eine Innentemperatur von 95  C auf dem Wasserbad erhitzt. Die Reaktionsmisehung wurde auf Eis gegossen und mit   Ammoniumhydroxyd    neutralisiert. Das sieh ausseheidende Öl wurde aus ¯thylacetat kristallisiert und   zweimal aus Isopropanol um-    kristallisiert.



   8 g von   a,    a-Diphenyl-y-diathylamino-valeramid (Smp. 161,   5-163     C) wurden in 150 ml   . ithanol    in einer Druckflasche gelöst, 10 g    Methyljodid zugegeben und die Mischung wäh-    rend 3 Stunden a. uf dem Wasserbad erhitzt.



  Die sich bei der Abkühlung   ausseheidenden    Kristalle wurden dreimal aus Methanol umkristallisiert.



   Das erhaltene quaternäre Jodid zeigte einen Smp. von 146-149¯ C.  



   PATENTANSPRUCH
Verfahren zur Herstellung eines quaternären   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 preparation of a new quaternary ammonium salt derived from a substituted phenylacetamide, which is characterized in that a compound of the formula
EMI1.1
 is reacted with methyl iodide. 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 product can be obtained in a known manner from the corresponding nitrile by hydrolytic conversion.



   example
30 g of α, α-diphenyl-γ-diethylamino-valeronitrile were mixed with 140 ml of concentrated sulfuric acid and 14 ml of water during
Hours heated 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 a, a-diphenyl-y-diethylamino-valeramide (melting point 161, 5-163 C) were in 150 ml. dissolved ithanol in a pressure bottle, added 10 g of methyl iodide, and a. Heated on a water bath.



  The crystals which separated out on cooling were recrystallized three times from methanol.



   The quaternary iodide obtained had a melting point of 146-149 ° C.



   PATENT CLAIM
Process for the preparation 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 Phenylacetamid abgeleiteten quaternären Ammoniumsalzes, das dadurch gekennzeichnet ist, dass eine Verbin dune der Formel EMI1.1 mit Methyl jodid umgesetzt wird. Die so hergestellte Verbindung soll zu pharmazeutischen Zweeken Verwendung finden. Process for the preparation of a quaternary ammonium salt The present invention relates to a process for the preparation of a new quaternary ammonium salt derived from a substituted phenylacetamide, which is characterized in that a compound of the formula EMI1.1 is reacted with methyl iodide. The compound thus produced is intended to be used for pharmaceutical purposes. Die antispasmodisehe Wirkung des so erhal tenen quaternären Ammoniumsalzes ist der jenigen der freien Base erheblich berlegen. 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 entspreehenden Nitril durch hydrolytische Umset-zlmg ewonnen werden. The base used as the starting product can be obtained in a known manner from the corresponding nitrile by hydrolytic conversion. Beispiel 30 g α, a-Diphenyl-y-diäthylamino-valero- nitril wurden mit 140 ml konzentrierter Sehwefelsäure und 14 ml Wasser während Stunden auf eine Innentemperatur von 95 C auf dem Wasserbad erhitzt. Die Reaktionsmisehung wurde auf Eis gegossen und mit Ammoniumhydroxyd neutralisiert. Das sieh ausseheidende Öl wurde aus ¯thylacetat kristallisiert und zweimal aus Isopropanol um- kristallisiert. example 30 g of α, α-diphenyl-γ-diethylamino-valeronitrile were mixed with 140 ml of concentrated sulfuric acid and 14 ml of water during Hours heated 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 von a, a-Diphenyl-y-diathylamino-valeramid (Smp. 161, 5-163 C) wurden in 150 ml . ithanol in einer Druckflasche gelöst, 10 g Methyljodid zugegeben und die Mischung wäh- rend 3 Stunden a. uf dem Wasserbad erhitzt. 8 g of a, a-diphenyl-y-diethylamino-valeramide (melting point 161, 5-163 C) were in 150 ml. ithanol dissolved in a pressure bottle, 10 g of methyl iodide added and the mixture for 3 hours a. Heated on a water bath. Die sich bei der Abkühlung ausseheidenden Kristalle wurden dreimal aus Methanol umkristallisiert. The crystals which separated out on cooling were recrystallized three times from methanol. Das erhaltene quaternäre Jodid zeigte einen Smp. von 146-149¯ C. The quaternary iodide obtained had a melting point of 146-149 ° C. PATENTANSPRUCH Verfahren zur Herstellung eines quaternären Ammoniumsalzes, dadurch gekennzeich- net, dass eine Verbindung der Formel EMI1.2 mit Methyljodid umgesetzt wird. PATENT CLAIM Process for the preparation of a quaternary ammonium salt, characterized in that a compound of the formula EMI1.2 is reacted with methyl iodide.
CH314215D 1949-11-07 1950-11-07 Process for the preparation of a quaternary ammonium salt CH314215A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US314215XA 1949-11-07 1949-11-07
CH307790T 1950-11-07

Publications (1)

Publication Number Publication Date
CH314215A true CH314215A (en) 1956-05-31

Family

ID=25735324

Family Applications (1)

Application Number Title Priority Date Filing Date
CH314215D CH314215A (en) 1949-11-07 1950-11-07 Process for the preparation of a quaternary ammonium salt

Country Status (1)

Country Link
CH (1) CH314215A (en)

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