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CH313316A - Process for the preparation of a new quaternary azacycloalkane compound - Google Patents

Process for the preparation of a new quaternary azacycloalkane compound

Info

Publication number
CH313316A
CH313316A CH313316DA CH313316A CH 313316 A CH313316 A CH 313316A CH 313316D A CH313316D A CH 313316DA CH 313316 A CH313316 A CH 313316A
Authority
CH
Switzerland
Prior art keywords
aza
bis
compound
preparation
new quaternary
Prior art date
Application number
Other languages
German (de)
Inventor
Karl Dr Miescher
Adrian Dr Marxer
Original Assignee
Ciba 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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH313316A publication Critical patent/CH313316A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic 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
    • C07D295/04—Heterocyclic 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
    • C07D295/12—Heterocyclic 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 singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic 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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic 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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

  

  verfahren zur Herstellung einer neuen     quaterniiren        Azacycloalkanverbindung       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung einer neuen       quaternären        Azaeyeloalkanverbindung,        wel-          ehes    dadurch gekennzeichnet ist, dass man       3-Metliy    1-3 -     aza        -pentylen-    (1, 5) -bis -     morpliolin     mit.

       Methyljodid    teilweise     quaternisiert.    Die  Umsetzung wird vorteilhaft in Anwesenheit  von Lösungsmitteln wie Alkohol oder     Aeeton          durehgeführt.     



  Das so erhaltene     3,N,N'-Trimethyl-3-aza-          pentylen    - (1,5) - bis -     morpholinium    -     dijodid     schmilzt bei 176-179 . Es besitzt spezifische  Wirkung auf die wichtigen     Regulationsmeeha-          nismen    des autonomen und Zentral-Nerven-         systems,    indem es die Funktion der Ganglien  blockiert, und soll als Heilmittel Verwendung  finden.  



  <I>Beispiel</I>  25,7     Gewiehtsteile        3-Methyl-3-aza-pentylen-          (1,5)-bis-morpholin    werden in 200     Volumtei-          len        abs.    Alkohol gelöst und unter Rühren 28,4       Gewiehtsteile        Methyljodid    in 50     Volumteilen          abs.    Alkohol     zugetropft.    Man erwärmt an  schliessend etwa 4 Stunden auf dem Wasser  bad und saugt nach dem Erkalten die gebil  deten Kristalle des     3,N,N'-Trimethyl-3-aza-          pentylen-(1,5)

  -bis-morpholinium-dijodids    der       Formel     
EMI0001.0036     
    ab.       Durch    Einengen der Mutterlauge und Zu  gabe von 100     Volumteilen    Essigester können  noch weitere Mengen der Verbindung erhal  ten werden. Die Kristalle schmelzen bei 176  bis 179 .    Das als Ausgangsmaterial verwendete       3-Methyl-    3 -     aza-pentylen-    (1,5     )-bis-morpholin     wird durch     Methylierung    des     3-Aza-pentylen-          (1,5)-bis-morpholins    mittels Formaldehyd und  Ameisensäure erhalten.



  Process for the Production of a New Quaternary Azacycloalkane Compound The subject of the present patent is a process for the production of a new quaternary azaeyeloalkane compound, which is characterized in that 3-Metliy 1-3 - aza-pentylen- (1,5) -bis - morpliolin With.

       Methyl iodide partially quaternized. The reaction is advantageously carried out in the presence of solvents such as alcohol or acetone.



  The 3, N, N'-trimethyl-3-aza-pentylene - (1,5) - bis - morpholinium - diiodide thus obtained melts at 176-179. It has a specific effect on the important regulatory mechanisms of the autonomic and central nervous system by blocking the function of the ganglia and is said to be used as a remedy.



  <I> Example </I> 25.7 parts by weight of 3-methyl-3-aza-pentylene- (1,5) -bis-morpholine in 200 parts by volume of abs. Dissolved alcohol and, with stirring, 28.4 parts by weight of methyl iodide in 50 parts by volume of abs. Alcohol added dropwise. It is then heated on the water bath for about 4 hours and, after cooling, the crystals of 3, N, N'-trimethyl-3-aza-pentylene- (1,5)

  -bis-morpholinium diiodides of the formula
EMI0001.0036
    from. By concentrating the mother liquor and adding 100 parts by volume of ethyl acetate, additional amounts of the compound can be obtained. The crystals melt at 176-179. The 3-methyl-3-aza-pentylene- (1,5) -bis-morpholine used as starting material is obtained by methylating 3-aza-pentylene- (1,5) -bis-morpholine with formaldehyde and formic acid.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung einer neuen quaternären Azaeyeloalkanverbindung, da- dureh gekennzeiebnet, dass man 3-Methyl- 3-aza-pentvlen-(1,5)-bis-morpholin mit. PATENT CLAIM A process for the production of a new quaternary azaeyeloalkane compound, since it is marked that 3-methyl-3-aza-pentvlene- (1,5) -bis-morpholine is used. Me- thyljodidteilweise quaternisiert. Das so erhaltene 3,N,1V\-Trimethyl-3-aza- pentylen - (1,5) - bis - morpholinium - dijodid sehmilzt bei 176-179 . Partly quaternized methyl iodide. The 3, N, 1V \ -trimethyl-3-aza-pentylene - (1.5) - bis - morpholinium - diiodide obtained in this way melts at 176-179. Es besitzt spezifisehe Wirkung auf die wiehtigen Regulationsmeeha- nismen des autonomen und Zentral-Nerven- systems, indem es die Funktion der Ganglien bloekiert, und soll als Heilmittel Verwendung finden. It has a specific effect on the important regulatory mechanisms of the autonomic and central nervous system by blocking the function of the ganglia and is said to be used as a remedy.
CH313316D 1953-03-06 1953-03-06 Process for the preparation of a new quaternary azacycloalkane compound CH313316A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH307135T 1953-03-06
CH313316T 1953-03-06

Publications (1)

Publication Number Publication Date
CH313316A true CH313316A (en) 1956-03-31

Family

ID=25735255

Family Applications (1)

Application Number Title Priority Date Filing Date
CH313316D CH313316A (en) 1953-03-06 1953-03-06 Process for the preparation of a new quaternary azacycloalkane compound

Country Status (1)

Country Link
CH (1) CH313316A (en)

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