CH297298A - Process for the preparation of a new quaternary salt. - Google Patents

Process for the preparation of a new quaternary salt.

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Publication number
CH297298A
CH297298A CH297298DA CH297298A CH 297298 A CH297298 A CH 297298A CH 297298D A CH297298D A CH 297298DA CH 297298 A CH297298 A CH 297298A
Authority
CH
Switzerland
Prior art keywords
sep
quaternary salt
preparation
new quaternary
new
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Cilag
Original Assignee
Cilag Ag
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 Cilag Ag filed Critical Cilag Ag
Publication of CH297298A publication Critical patent/CH297298A/en

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  • Pyridine Compounds (AREA)

Description

  

      verfahren    zur Herstellung     eines    neuen     quaternären    Salzes.         (tegenstand    der     Erfindung    ist ein Ver  fahren zur     Herstellung    eines neuen     quater-          nären    Salzes der Formel  
EMI0001.0009     
    welches dadurch gekennzeichnet ist, dass man  die Verbindung der Formel  
EMI0001.0010     
    mit     Methansulfonsäure-methylester        quaterni-          siert.     



  Der Umsatz     gesehieht    vorzugsweise in An  wesenheit eines     Lösimgs-    bzw. Verdünnungs  mittels.  



  Bei Verwendung von 1     Mol        Methansulfon-          eäure-methylester    auf 1     Mül    der Verbindung I         wurde    die     Beobaehtung    gemacht, dass das ter  tiäre     Stiekstoffatom    der Seitenkette vor dem       Stickstoffatom    des     Pyridinringes        quaternisiert     wird.

   Es ist wichtig, dass man nicht mit einem  zu grossen     Übersehuss    an     Methansulfonsäure-          methylester    arbeitet, da sonst die Gefahr be  steht, dass das     Pyridinstickstoffatom    auch       quaternisiert    wird. Das so erhaltene     Nicotin-          säure-NT-(1,2-diphenyl-äthyl)-N        -(2'-dimethyl-          amino-äthyl)        -amid-N-methyl-methansulfonat     ist ein leicht wasserlösliches Salz, welches bei  205 bis 206  schmilzt.  



  <I>Beispiel:</I>  10 g     Nicotinsäure-N-(1,2-diphen3rl-äthyl)-          N-(2'-dimethylamino-äthyl)-amid    werden in  60     em3    Essigester gelöst und mit. 3 g     Methan-          sulfonsäure-methylester    versetzt. Das     Reak-          tionsgemiseh    wird eine Stunde     -unter    Rühren  am     Rückfluss    gekocht. Nach dem Abkühlen  wird mit 170     cm3    Wasser versetzt,     ausgeäthert,     mit Kohle filtriert     und    bei 65  das Wasser ab  destilliert.

   Der Rückstand. wird 24     Stunden     bei 60 bis 70  über     Phosphorpentoxyd    ge  trocknet, dann in 100     cm3    Chloroform aufge  nommen und mit 200     em3    Äther versetzt. Das  erhaltene Produkt wird darauf aus     Ace-          ton/Äthanol    umkristallisiert, wobei man 63     %     des bei 205 bis     206     schmelzenden Nicotin       säure-N-(1,2-diphenyl-äthyl)-N-(2'-dimethyl-          amino    -     äthyl)    -     amid-N-methyl-methansulfonats     gewinnt. Die Verbindung löst sieh leicht in  Wasser.



      process for the production of a new quaternary salt. (The subject of the invention is a process for the production of a new quaternary salt of the formula
EMI0001.0009
    which is characterized in that the compound of the formula
EMI0001.0010
    quaternized with methanesulfonic acid methyl ester.



  The conversion is preferably seen in the presence of a solvent or diluent.



  When using 1 mol of methyl methanesulfonate to 1 mol of compound I, it was observed that the tertiary nitrogen atom of the side chain is quaternized before the nitrogen atom of the pyridine ring.

   It is important not to work with too large an excess of methyl methanesulfonate, as otherwise there is a risk that the pyridine nitrogen atom will also be quaternized. The nicotinic acid-NT- (1,2-diphenyl-ethyl) -N - (2'-dimethyl-amino-ethyl) -amide-N-methyl-methanesulfonate obtained in this way is a readily water-soluble salt, which at 205 to 206 melts.



  <I> Example: </I> 10 g of nicotinic acid-N- (1,2-diphen3rl-ethyl) -N- (2'-dimethylamino-ethyl) -amide are dissolved in 60 cubic meters of ethyl acetate and mixed with. 3 g methanesulfonic acid methyl ester are added. The reaction mixture is refluxed with stirring for one hour. After cooling, 170 cm3 of water are added, the mixture is etherified, filtered with charcoal and the water is distilled off at 65.

   The residue. is dried over phosphorus pentoxide for 24 hours at 60 to 70, then taken up in 100 cm3 of chloroform and mixed with 200 cubic meters of ether. The product obtained is then recrystallized from acetone / ethanol, 63% of the nicotinic acid-N- (1,2-diphenyl-ethyl) -N- (2'-dimethyl-amino-ethyl) melting at 205 to 206 - amide-N-methyl-methanesulfonate wins. The compound dissolves easily in water.

Claims (1)

PATENT A-'SPRIJCH Verfahren zur Herstellung eines neuen quaternären Salzes der Formel EMI0002.0003 dadureh gekennzeiehnet, dass man die Verbin dung der Formel EMI0002.0006 EMI0002.0007 mit <SEP> JIethansulfon@äure-meths-le@ter <SEP> quaterni siert. PATENT A-'SPRIJCH Process for the preparation of a new quaternary salt of the formula EMI0002.0003 denzeiehnet that one is the compound of the formula EMI0002.0006 EMI0002.0007 quaternized with <SEP> JIethansulfon @ äure-meths-le @ ter <SEP>. <SEP> Das <SEP> so <SEP> erhaltene <SEP> Nieotinsäure--.\L--(1,2 diphen <SEP> z <SEP> 1-äthy1) <SEP> - <SEP> N <SEP> - <SEP> diniethz <SEP> lamino <SEP> - <SEP> äthy1) <SEP> ainid-N-methi <SEP> l-inetlian-sulfonat <SEP> bildet <SEP> weisse, <tb> leieht <SEP> wasserlösliehe <SEP> Kristalle, <SEP> die <SEP> bei <SEP> 205 <SEP> bis <tb> 206 <SEP> sehmelzen. <tb> Die <SEP> neue <SEP> Verbindung <SEP> soll <SEP> als <SEP> Spasmolyti kum <SEP> und <SEP> als <SEP> Zwisehenprodukt <SEP> Verwendung <tb> finden. <SEP> The <SEP> so <SEP> obtained <SEP> nieotinic acid -. \ L - (1,2 diphen <SEP> z <SEP> 1-ethy1) <SEP> - <SEP> N <SEP> - <SEP> diniethz <SEP> lamino <SEP> - <SEP> äthy1) <SEP> ainid-N-methi <SEP> l-inetlian-sulfonate <SEP> forms <SEP> white, <tb> contains <SEP> water-soluble <SEP> crystals, <SEP> the <SEP> at <SEP> 205 <SEP> to <tb> 206 <SEP> sehmelzen. <tb> The <SEP> new <SEP> connection <SEP> should use <SEP> as <SEP> spasmolytic <SEP> and <SEP> as <SEP> interim product <SEP> <tb> find.
CH297298D 1951-03-01 1951-03-01 Process for the preparation of a new quaternary salt. CH297298A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH297298T 1951-03-01
CH294512T 1951-03-01

Publications (1)

Publication Number Publication Date
CH297298A true CH297298A (en) 1954-03-15

Family

ID=25733495

Family Applications (1)

Application Number Title Priority Date Filing Date
CH297298D CH297298A (en) 1951-03-01 1951-03-01 Process for the preparation of a new quaternary salt.

Country Status (1)

Country Link
CH (1) CH297298A (en)

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