CH328671A - Process for the production of a new basic substituted fatty acid-2-halogen-6-methyl-anilide - Google Patents

Process for the production of a new basic substituted fatty acid-2-halogen-6-methyl-anilide

Info

Publication number
CH328671A
CH328671A CH328671DA CH328671A CH 328671 A CH328671 A CH 328671A CH 328671D A CH328671D A CH 328671DA CH 328671 A CH328671 A CH 328671A
Authority
CH
Switzerland
Prior art keywords
methyl
anilide
halogen
fatty acid
production
Prior art date
Application number
Other languages
German (de)
Inventor
Henry Dr Martin
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 CH328671A publication Critical patent/CH328671A/en

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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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 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
    • C07D295/15—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 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 to an acyclic saturated chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Verfahren    zur     Herstellung    eines neuen basisch substituierten       Fettsäure-2-halogen-6-methyl-anilids            Gegenstand    des vorliegenden     J'atentes    bil  det ein Verfahren zur     -Herstellung    eines neuen  basisch substituierten     F'ettsäure-2-halogen-6-          methy1,-anilids,        welches,    dadurch gekennzeich  net ist., dass man eine     Verbindung    der Formel  
EMI0001.0011     
    in welcher X einen     reaktionsfähigen,    wäh  rend' der Reaktion sich abspaltenden Rest  bedeutet,

       mit        Pyrrolidnn    umsetzt.  



  Der Rest X kann in einem Halogenatom  oder einem sonstigen für den Austausch  gegen den basischen Rest geeigneten reak  tionsfähigen     Substituenten,    wie zum Beispiel  einer     Alkylsulfonyloxy-    oder     Arylsulfonyl-          oxygruppe,    bestehen.

   Der Austausch der  Gruppe X gegen den     Pyrrolidinrest    erfolgt  zum Beispiel durch     einfaches        Erwärmen    mit       Pyrrolidin,    gegebenenfalls     in    Gegenwart       eines:        basisch        reagierenden        Kondensationsmit-          tels    oder von     Pyrrolidin    im Überschuss.  



  Das     Pyrrolidinoacetat-N-methyl-2-chlor    -     6-          methyl-anilid        ist    ein farbloses, unter 0,05 mm       Hg    bei     1'23    bis 125  siedendes     j911.        Das    neue       Anilid    soll als     Lokalanästhetikum    und als       Zwischenprodukt    zur     Herstellung    weiterer  Derivate Verwendung finden.

      <I>Beispiel</I>  23 Gewichtsteile     Chloracet    - N -     methyl-2-          chlor-6-methyl-anäid        (gewonnen    durch Um  setzen von     N-Methyl-2'-cblior        -:6    -     methyl-anilin     mit     Chloracetylchlorid    in Gegenwart von Na  triumacetat) werden in 4'0     Gewichtsteilen     Äthanol suspendiert und mit 20 Gewichts  teilen     Pyrrolidin    versetzt. Die Temperatur  steigt dabei leicht an, und ein grosser Teil,  des Reaktionsgemisches geht in Lösung.

   Nun  wird     während    4     Stunden    bei Zimmertem  peratur gerührt,     dann    3     'Stunden    bei 45  bis 50  und     endlich    4 Stunden bei 65 bis 75 .  Mit     Wasserdampf        wird    hierauf der Alkohol ,       und    das überschüssige     Pyrrolidin    abgeblasen       und    nach dem Erkalten das zurückbleibende  Öl in Äther aufgenommen.

   Nach dem Trock  nen der ätherischen     Lösung    und Verjagen       des        Lösungsmittels        verbleibt        ein.    Öl, das durch       Vacuumdestillation    gereinigt wird. Man er  hält 22     Gewichtsteile    reines     Pyrrolidinoessig-          säure-N-methyl-9        chlor    - 6 -     methyl-anilid.    Die  Umsetzung mit.     Pyrrolidin        kann    auch in Benzol  stattfinden.



      Process for the production of a new basic substituted fatty acid-2-halogen-6-methyl-anilide The subject of the present patent forms a process for the production of a new basic-substituted fatty acid-2-halogen-6-methyl-anilide, which is characterized in that one is a compound of the formula
EMI0001.0011
    in which X means a reactive radical that is split off during the reaction,

       with Pyrrolidnn implemented.



  The radical X can consist of a halogen atom or another reactive substituent suitable for replacement with the basic radical, such as an alkylsulfonyloxy or arylsulfonyloxy group.

   The group X is exchanged for the pyrrolidine residue, for example, by simple heating with pyrrolidine, if appropriate in the presence of a basic condensing agent or an excess of pyrrolidine.



  The pyrrolidinoacetate-N-methyl-2-chloro-6-methyl-anilide is a colorless j911 that boils below 0.05 mm Hg at 1'23 to 125. The new anilide is to be used as a local anesthetic and as an intermediate product for the production of further derivatives.

      <I> Example </I> 23 parts by weight of chloroacet - N - methyl-2-chloro-6-methyl-anaide (obtained by reacting N-methyl-2'-cblior -: 6 - methyl-aniline with chloroacetyl chloride in the presence of sodium acetate) are suspended in 4'0 parts by weight of ethanol and treated with 20 parts by weight of pyrrolidine. The temperature rises slightly, and a large part of the reaction mixture goes into solution.

   The mixture is then stirred for 4 hours at room temperature, then for 3 hours at 45 to 50 and finally for 4 hours at 65 to 75. The alcohol and the excess pyrrolidine are then blown off with steam and, after cooling, the remaining oil is taken up in ether.

   After the ethereal solution has dried and the solvent has been driven off, a remains. Oil that is purified by vacuum distillation. He keeps 22 parts by weight of pure pyrrolidinoacetic acid N-methyl-9 chloro - 6 - methyl anilide. Implementation with. Pyrrolidine can also take place in benzene.

Claims (1)

P A TFNT A N9iPR.TTnH Verfahren zur Herstellung eines neuen basisch substituierten Pettsäure-2-halogen-6- methyl-anilids, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0002.0001 in welcher X -einen reaktionsfähigen wäh rend der Reaktion sich übspa'ltenden Rest bedeutet, P A TFNT A N9iPR.TTnH Process for the preparation of a new basic substituted fatty acid-2-halogen-6-methyl-anilide, characterized in that a compound of the formula EMI0002.0001 in which X - means a reactive residue that overlaps during the reaction, mit Pyrrolidin umsetzt. Das auf diese Weise erhaltene Pyrrolidinoacet-N-me- thyl-2-chlor-6-methyl-anili:d, bildet ein farb loses, unter 0,05 mm I-Ig bei 123 bis 1'25 sie dendes Öl. UNTERANSPRUCH Verfahren nach Patentanspruch, dadurch gekennzeichnet., dass man ein Halogenacet-N- methyl-2-chlor-G-methyl-anilild mit Pyrrolidin reagieren lässt. Reacts with pyrrolidine. The pyrrolidinoacet-N-methyl-2-chloro-6-methyl-anili: d obtained in this way forms a colorless oil which sinks below 0.05 mm I-Ig at 123 to 1'25. SUBCLAIM Process according to patent claim, characterized in that a haloacet-N-methyl-2-chloro-G-methyl-anilild is allowed to react with pyrrolidine.
CH328671D 1952-11-25 1952-11-25 Process for the production of a new basic substituted fatty acid-2-halogen-6-methyl-anilide CH328671A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH307799T 1952-11-25
CH328671T 1952-11-25

Publications (1)

Publication Number Publication Date
CH328671A true CH328671A (en) 1958-03-15

Family

ID=25735447

Family Applications (1)

Application Number Title Priority Date Filing Date
CH328671D CH328671A (en) 1952-11-25 1952-11-25 Process for the production of a new basic substituted fatty acid-2-halogen-6-methyl-anilide

Country Status (1)

Country Link
CH (1) CH328671A (en)

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