CH292702A

CH292702A - Process for the preparation of a new quaternary ammonium compound.

Info

Publication number: CH292702A
Authority: CH
Inventors: Aktiengesellschaft Ciba
Original assignee: Ciba Geigy
Priority date: 1949-02-15
Filing date: 1949-02-15
Publication date: 1953-08-15

Description

  

  Verfahren zur     Herstellung    einer neuen     quaternären        Ammoniumverbindung.            Ge        lenstand    des vorliegenden Patentes ist       ein    Verfahren zur Herstellung einer neuen       quaternären        Ammoniumverbindung,    welches  dadurch     --ekennzeiehnet    ist,     dass    man     N,N,N',     N',     3-Pentamethyl-3-aza-pentaai-1,5-diamin    mit       1)iniet.liylstilfat    teilweise     quaternisiert.    Die       1"insetziin--,

      wild vorteilhaft in Anwesenheit  von     Lösungsmitteln,    wie Alkohol oder Aceton,       durehg-eführt.     



  Das so erhaltene     neue        NT,N,N,NT',N',N',3-          1iept@iniethyl    - 3 -     aza    -     pentan-1,5        -diammonium-          di-inetlivlsulfat    bildet äusserst     zerfliessliehe,     an der Luft begierig Wasser anziehende     Kri-          stalle,    die bei 85 bis 87  schmelzen.

   Es besitzt       slic@zü'ische    Wirkung auf die wichtigen     Regu-          lationsmeehanismen    des autonomen     Lund    Zen-         tral-Nerveilsystems,    indem es die Funktion der  Ganglien blockiert,     i        id    kann als Heilmittel  Verwendung finden.

      <I>Beispiel:</I>  17,3 Gewichtsteile     N,N,N',N',3-Pentamethyl-          3-aza=pentan-1,5-diamin    in 75     Volumteilen        abs.     Alkohol werden nach und nach mit 25,2 Ge  wichtsteilen     Dimethylsulfat    in 25     Volumteilen          abs.    Alkohol versetzt     Lund    nachher 3     Stunden     unter     Rüekfluss    erhitzt.

   Man verdampft zur  Trockne und fällt den Rückstand um durch  Lösen in Alkohol     und    Versetzen mit Essig  ester und erhält so das       Heptamethyl-3-aza-pentan-1,5-diammonium-          di-methylsulfat    der Formel  
EMI0001.0048     
         1)ic    Verbindung bildet, äusserst     zerfliessliche,     an     der    Luft begierig wasseranziehende Kri  stalle, die bei 85 bis 87  schmelzen.  



  Zur Herstellung des     N,N,N',N',3-Penta-          meiliyl-3-aza-pentan-7.,5-diamins    kann man das       3-:lza-pentan-7.,5-diamin    mittels wässeriger       Fornialdehydlösung    und Ameisensäure     methy-          1        iereu.  



  Process for the preparation of a new quaternary ammonium compound. The subject matter of the present patent is a process for the preparation of a new quaternary ammonium compound, which is identified by the fact that N, N, N ', N', 3-pentamethyl-3-aza-pentaai-1,5-diamine are mixed with 1) iniet.liylstilfat partially quaternized. The 1 "insetziin--,

      wildly advantageous in the presence of solvents such as alcohol or acetone.



  The new NT, N, N, NT ', N', N ', 3-1iept @ iniethyl - 3 - aza - pentane-1,5-diammonium di-inietal sulfate thus obtained forms extremely deliquescent water, which is greedy in the air Crystals that melt at 85 to 87.

   It has a slic @ zü'ic effect on the important regulatory mechanisms of the autonomic central and nervous system by blocking the function of the ganglia, i id can be used as a remedy.

      <I> Example: </I> 17.3 parts by weight of N, N, N ', N', 3-pentamethyl-3-aza = pentane-1,5-diamine in 75 parts by volume of abs. Alcohol are gradually abs with 25.2 parts by weight Ge dimethyl sulfate in 25 parts by volume. Lund then added alcohol and heated it under reflux for 3 hours.

   It is evaporated to dryness and the residue is reprecipitated by dissolving in alcohol and adding ethyl acetate to give heptamethyl-3-aza-pentane-1,5-diammonium dimethyl sulfate of the formula
EMI0001.0048
         1) The compound forms extremely deliquescent crystals, which are greedy for water in the air and which melt at 85 to 87.



  To prepare the N, N, N ', N', 3-pentameiliyl-3-aza-pentane-7, 5-diamine, the 3-: lza-pentane-7, 5-diamine can be obtained by means of an aqueous formaldehyde solution and methyl formic acid.

Claims

PATENT CLAIM Process for the production of a new iluaternä.ren ammonium compound, characterized in that N, N, N ', N', 3-pentamethyl-3-aza-pentane-1,5-diamine is partially quaternized with dimethyl sulfate. The new N, N, N, N ', N', N ', 3-hepta-methyl-3-aza-pentane-1,5-diammonium-di-methyl sulfate thus obtained forms extremely deliquescent, water-attracting crystals in the air stalls,

which melt at 85 to 87. 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 can be used as a remedy.