CH314211A - Process for the preparation of a quaternary ammonium salt - Google Patents

Process for the preparation of a quaternary ammonium salt

Info

Publication number
CH314211A
CH314211A CH314211DA CH314211A CH 314211 A CH314211 A CH 314211A CH 314211D A CH314211D A CH 314211DA CH 314211 A CH314211 A CH 314211A
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 CH314211A publication Critical patent/CH314211A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (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 da  durch     gekennzeichnet        ist,    dass eine Verbin  dung der Formel  
EMI0001.0010     
    mit     Methyljodid    umgesetzt wird. Die so her  gestellte Verbindung soll zu pharmazeutischen  Zwecken Verwendung finden.  



  Die antispasmodische Wirkung des so er  haltenen     quaternären        Ammoniumsalzes    ist  derjenigen der freien Base erheblich über  legen. Im weiteren kommt dem Salz auch eine       mydriatische    Wirksamkeit zu.  



  Die     als    Ausgangsprodukt verwendete Base  kann in bekannter Weise aus dem     entspre-          ehenden        Nitril    durch     hydrolytische    Umsetzung  gewonnen werden.  



  <I>Beispiel</I>  22 g     a;a-Diphenyl-b-piperidino-valeronitril     wurden mit 140     m1    konzentrierter Schwefel  säure und 14     mal    Wasser während 4 Stunden  auf eine Innentemperatur von 95  C auf dem  Wasserbad erhitzt. Die     Reaktionsmischung       wurde hierauf auf Eis     gegossen    und     mit    Am  moniumhydroxyd     neutralisiert.    Das entstan  dene Öl wurde aus     Äthylacetat        kristallisiert     und aus     Isopropanol        umkristallisiert.     



  8,5 g     a;a-Diphenyl-8-piperidino-valeronitril          (Smp.119-120     C)     wurden.    in 150     ml        Äthanol     in einer Druckflasche gelöst, 10g     Methyljodid     zugegeben und die Mischung auf dem     Wasser-          bad    während 3 Stunden erwärmt.

   Die     Kristalle,     die sich beim     Abkühlen    bildeten,     wurden    aus  Methanol     umkristallisiert.    Das erhaltene     qua-          ternäre        Jodid    zeigte einen     Schmelzpunkt    von       218-219     C.



  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 which is derived from a substituted phenyl acetamide and which is characterized in that a compound of the formula
EMI0001.0010
    is reacted with methyl iodide. The compound thus established is intended to be used for pharmaceutical purposes.



  The antispasmodic effect of the quaternary ammonium salt thus obtained 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.



  <I> Example </I> 22 g of a; a-diphenyl-b-piperidino-valeronitrile were heated with 140 ml of concentrated sulfuric acid and 14 times water for 4 hours to an internal temperature of 95 C on a water bath. The reaction mixture was then poured onto ice and neutralized with ammonium hydroxide. The resulting oil was crystallized from ethyl acetate and recrystallized from isopropanol.



  8.5 g of a; a-diphenyl-8-piperidino-valeronitrile (m.p. 119-120 C) were. Dissolve in 150 ml of ethanol in a pressure bottle, add 10 g of methyl iodide and heat the mixture on a water bath for 3 hours.

   The crystals that formed on cooling were recrystallized from methanol. The quaternary iodide obtained had a melting point of 218-219 C.

 

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines quater- nären Ammoniumsalzes, dadurch gekennzeich net, dass eine Verbindung der Formel EMI0001.0052 mit Methyljodid umgesetzt wird. PATENT CLAIM Process for the production of a quaternary ammonium salt, characterized in that a compound of the formula EMI0001.0052 is reacted with methyl iodide.
CH314211D 1949-11-07 1950-11-07 Process for the preparation of a quaternary ammonium salt CH314211A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US314211XA 1949-11-07 1949-11-07
CH307790T 1950-11-07

Publications (1)

Publication Number Publication Date
CH314211A true CH314211A (en) 1956-05-31

Family

ID=25735320

Family Applications (1)

Application Number Title Priority Date Filing Date
CH314211D CH314211A (en) 1949-11-07 1950-11-07 Process for the preparation of a quaternary ammonium salt

Country Status (1)

Country Link
CH (1) CH314211A (en)

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