CH311547A - 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
CH311547A
CH311547A CH311547DA CH311547A CH 311547 A CH311547 A CH 311547A CH 311547D A CH311547D A CH 311547DA CH 311547 A CH311547 A CH 311547A
Authority
CH
Switzerland
Prior art keywords
methyl
anilide
halogen
fatty acid
chloro
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 CH311547A publication Critical patent/CH311547A/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
    • C07D295/14—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Description

  

  Verfahren zur Herstellung eines neuen basisch substituierten     Fettsäure-          (2-halogen-6-methyl-anilids).       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines neuen       basiseh    substituierten     PettsäLue-(2-halogen-6-          rnethyl-anilids),    welches dadurch     gekennzeieh-          net    ist. dass man auf eine     Verbindunz    der    Formel  
EMI0001.0009     
    eine Verbindung der Formel  
EMI0001.0010     
    in welchen Formeln X     und    Y reaktionsfähige,  bei der Reaktion sich abspaltende Reste be  deuten, einwirken lässt.  



  Als Verbindungen der     Formel    1 kommen  für einen Umsatz beispielsweise in Frage:       2-Chlor-6-methyl-anilin,    eventuell in Form sei  ner Salze, wie des Hydrochlorids oder des  Sulfates, weiter die     N-Halogen-magnesyl-Ver-          bindungen    (X=     Mg.Hal)usf.     



  Als Verbindungen der Formel     II    kommen  beispielsweise in Frage:     ss-(2-l,lethyl-piperi-          dino)-buttersäure    selbst und ihre     reaktions-          i    fähigen funktionellen Derivate wie ihre Halo  benide, ihre Ester, ihre Aashydride, beispiels  weise die reinen und auch die gemischten  Aashydride mit Phosphorsäure, Schwefel  säure und Kohlensäure     usf.       Man kann beispielsweise     2-Chlor-6-methyl-          anilin    oder auch ein Salz desselben in Gegen  wart eines für diese Zwecke geeigneten was  serabspaltenden Mittels wie     Phosphorpent-          oxyd,

          Phosphoroxychlorid        usf.    mit     ss-(2-Me-          thyl-piperidino)-buttersäure    behandeln.  



  Weiter kann man auch     2-Chlor-6-methyl-          anilin    bzw. ein     Salz    desselben mit einem ss-(2  Methyl-piperidino)-buttersäurehalogenid (bzw.  einem     Salz    eines solchen) oder einem     Aashy-          drid    zur Reaktion bringen.  



  Es ist weiterhin auch möglich,     2-Chlor-6-          methyl-anilin    mit einem     6-(2-Methyl-piperi-          dino)    -     buttersäureester,        vorzugsweise    einem       Arylester,    bei erhöhter Temperatur zu     acylie-          ren    oder beispielsweise ein     Halogen-magne-          syl-2-chlor-6-methyl-anilin    (erhalten durch  Umsetzen der Base     mit    einem     Alkylmagne-          siumhalid)    mit einem     ss-(2-1Zethyl-pipeiidino)

  -          buttersäurealkylester        umzusetzen.     



  Das auf diese Weise erhaltene     ss-(2-Methyl-          pip        eridino)    - Buttersäure - (T- chlor -     6'-        methyl-          anilid)    bildet ein farbloses, bei 126-128   schmelzendes Kristallpulver. Das neue     Anilid     soll als Lokalanästhetikum und als Zwischen  produkt zur Herstellung weiterer Derivate  Verwendung finden.  



  <I>Beispiel:</I>  25 Gewichtsteile     fl-(2-Methyl-piperidino)-          buttersäureehlorid    -     hydrochlorid    in     Benzol     werden mit einer Mischung von 14 Gewichts  teilen     2-Chlor-6-methyl-anilin    und 20     Ge-          wiehtsteilen        Triäthylamin    erwärmt. Anschlie-           ssend    wird das gebildete     Triäthylaminhydro-          chlorid    durch Ausschütteln mit Wasser ent  fernt und die     Benzollösung    nach dem Trock  nen verdampft.

   Der Rückstand stellt das     ss-(2-          Methyl-piperidino)-buttersäure-        (2'-chlor-6'-          methyl-anilid)    dar, das durch Umkristallisa  tion aus     Petroläther    gereinigt werden kann.  



  Die Reaktion kann auch ohne     Verdün-          nungs-    und Kondensationsmittel durchgeführt  werden, indem man beispielsweise das ss-(2       l1eth-rl-piperidino)-buttersäurechlorid-hydro-          chlorid    mit     2-Chlor-6-methyl-anilin    trocken er  hitzt, anschliessend die Reaktionsmasse mit  Wasser verdünnt und in üblicher Weise auf  arbeitet.



  Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). The subject of the present patent is a process for the production of a new basic substituted PettsäLue- (2-halogen-6-methyl-anilide), which is marked thereby. that one is on a connection of the formula
EMI0001.0009
    a compound of the formula
EMI0001.0010
    in which formulas X and Y are reactive residues that are split off during the reaction.



  Compounds of formula 1 that can be used for conversion include, for example: 2-chloro-6-methyl-aniline, possibly in the form of its salts, such as the hydrochloride or sulfate, and the N-halo-magnesyl compounds (X = Mg.Hal) etc.



  As compounds of the formula II, for example: ss- (2-l, lethyl-piperidino) -butyric acid itself and its reactive functional derivatives such as its halo benide, its esters, its aashydrides, for example the pure and also the mixed aashydrides with phosphoric acid, sulfuric acid and carbonic acid etc. You can, for example, 2-chloro-6-methylaniline or a salt thereof in the presence of a water-releasing agent such as phosphorus pentoxide,

          Treat phosphorus oxychloride, etc. with ss- (2-methylpiperidino) butyric acid.



  Furthermore, 2-chloro-6-methyl-aniline or a salt thereof can also be reacted with an β- (2-methyl-piperidino) -butyric acid halide (or a salt of such) or an aashydride.



  It is furthermore also possible to acylate 2-chloro-6-methyl-aniline with a 6- (2-methyl-piperidino) -butyric acid ester, preferably an aryl ester, or, for example, a halo-magnetosyl -2-chloro-6-methyl-aniline (obtained by reacting the base with an alkylmagnesium halide) with an ss- (2-1Zethyl-pipeiidino)

  - to implement butyric acid alkyl ester.



  The ss- (2-methylpiperidino) - butyric acid - (T-chloro - 6'-methylanilide) obtained in this way forms a colorless crystal powder that melts at 126-128. The new anilide is to be used as a local anesthetic and as an intermediate product for the manufacture of other derivatives.



  <I> Example: </I> 25 parts by weight of fl- (2-methyl-piperidino) butyric acid chloride hydrochloride in benzene are heated with a mixture of 14 parts by weight of 2-chloro-6-methyl-aniline and 20 parts by weight of triethylamine . The triethylamine hydrochloride formed is then removed by shaking with water and the benzene solution is evaporated after drying.

   The residue is the ss- (2-methyl-piperidino) -butyric acid (2'-chloro-6'-methyl-anilide), which can be purified by recrystallization from petroleum ether.



  The reaction can also be carried out without a diluent and condensation agent, for example by heating the ss- (2 l1eth-rl-piperidino) butyric acid chloride hydrochloride dry with 2-chloro-6-methyl-aniline, followed by the Reaction mass diluted with water and works in the usual way.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6- methyl-anilids), dadurch gekennzeichnet, dass man auf eine Verbindung der Formel EMI0002.0017 eine Verbindung der Formel EMI0002.0018 in welchen Formeln X und Y reaktionsfähige, bei der Reaktion sich abspaltende Reste be deuten, einwirken lässt. PATENT CLAIM Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-anilide), characterized in that one is based on a compound of the formula EMI0002.0017 a compound of the formula EMI0002.0018 in which formulas X and Y are reactive residues that are split off during the reaction. Das auf diese Weise erhaltene ss-(2-Methy1- pip eridino) -buttersäure - (2-ehlor-6-methy 1-ani- lid) ist ein farbloses, bei 126-128 schmel zendes Kristallpulver. Das neue Anilid soll als Lokalanästhetikum und als Zwischenpro dukt Verwendung finden. The ss- (2-methy1-pip eridino) -butyric acid - (2-chloro-6-methy 1-anilide) obtained in this way is a colorless crystal powder melting at 126-128. The new anilide will be used as a local anesthetic and as an intermediate product. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man 2-Chlor-6-methyl- anilin mit einem ss-(2-lblethyl-piperidino)-but- tersäurehalogenid umsetzt. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that 2-chloro-6-methyl-aniline is reacted with an β- (2-methyl-piperidino) -butyric acid halide.
CH311547D 1952-02-25 1952-02-25 Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). CH311547A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311547T 1952-02-25
CH306201T 1955-03-31

Publications (1)

Publication Number Publication Date
CH311547A true CH311547A (en) 1955-11-30

Family

ID=25735074

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311547D CH311547A (en) 1952-02-25 1952-02-25 Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).

Country Status (1)

Country Link
CH (1) CH311547A (en)

Similar Documents

Publication Publication Date Title
CH311547A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311544A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311546A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311535A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311540A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311537A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311551A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311541A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311549A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311545A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311534A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311550A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311538A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311542A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311533A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311536A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311558A (en) Process for the production of a new basic substituted fatty acid amide.
CH311532A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311565A (en) Process for the production of a new basic substituted fatty acid amide.
CH306201A (en) Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methylanilide).
CH311564A (en) Process for the production of a new basic substituted fatty acid amide.
CH311539A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311552A (en) Process for the production of a new basic substituted fatty acid amide.
CH311548A (en) Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311562A (en) Process for the production of a new basic substituted fatty acid amide.