CH311563A - Process for the production of a new basic substituted fatty acid amide. - Google Patents

Process for the production of a new basic substituted fatty acid amide.

Info

Publication number
CH311563A
CH311563A CH311563DA CH311563A CH 311563 A CH311563 A CH 311563A CH 311563D A CH311563D A CH 311563DA CH 311563 A CH311563 A CH 311563A
Authority
CH
Switzerland
Prior art keywords
fatty acid
acid amide
substituted fatty
production
new basic
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 CH311563A publication Critical patent/CH311563A/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
    • 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

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  • 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     Fettsäureamides.            Gegenstand    des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines neuen  basisch substituierten     Fettsäureamides,    wel  ches dadurch gekennzeichnet ist, dass man auf  eine Verbindung der Formel  
EMI0001.0004     
    eine Verbindung der Formel  
EMI0001.0005     
    in welchen Formeln X und Y reaktionsfähige.  bei der Reaktion sich abspaltende Reste be  deuten, einwirken lässt.  



  Als Verbindungen der Formel I kommen  für einen Umsatz beispielsweise in Frage:  Das freie Amin (Y = H), aber auch dessen  Salze, wie beispielsweise das     Hydroehlorid     oder das Sulfat.  



  Als Verbindungen der Formel     II    kommen  beispielsweise in Frage:     2,5-Dimethyl-pyrro-          lidino-essigsäure    selbst und ihre     reaktions-          iä.higen    funktionellen Derivate wie ihre Halo  genide, ihre Ester, ihre     Anhydride,    beispiels  weise die reinen und auch die gemischten       i        Anhydride    mit Phosphorsäure, Schwefelsäure  und Kohlensäure     usf.     



  Man kann beispielsweise     N-(2-Phenoxy-          äthyl-1)        -N-methylamin    oder auch ein Salz des  selben in Gegenwart eines für diese Zwecke    geeigneten wasserabspaltenden Mittels wie       Phosphorpentoxyd,        Phosphoroxychlorid        usf.     mit     2,5-Dimethyl-pyrrolidino-essigsäure    be  handeln.  



  Weiter kann man auch     N-(2-Phenoxy-          äthyl-l)        -N-methylamin    bzw. ein     Salz    dessel  ben mit einem     2,5-Dimethylamin-pyrrolidino-          essigsäure-halogenid    (bzw. einem Salz eines  solchen) oder einem     Anhydrid    zur Reaktion  bringen.  



  Es ist     weiterhin    auch möglich,     N-(2-Phen-          oxy-äthyl-1)-N-methylamin    mit einem     2,5-Di-          methyl-pyrrolidino-essigsäureester,    vorzugs  weise einem     Arylester,    bei erhöhter Tempera  tur zu     acylieren.     



  Das auf diese Weise erhaltene N-(2-Phen       oxy-äthyl-1)-N-methyl-2',5'-dimethyl-pyrroli-          dino-acetamid    bildet ein farbloses, unter  0,08 mm bei 150-151  siedendes Öl.  



  Das neue     Amid    soll als Lokalanästhetikum  und als Zwischenprodukt zur Herstellung wei  terer Derivate Verwendung finden.  



  <I>Beispiel:</I>  15,2 g N-     (2-Phenoxy-äthyl-1)-N-methylamin     in Benzol werden mit einer Mischung von  20 g     2,5-Dimethyl-pyrrolidino-essigsäurechlo-          rid-hydrochlorid        und    20 Gewichtsteilen     Tri-          äthylamin    erwärmt. Anschliessend wird das  gebildete     Triäthylaminhydrochlorid    durch  Ausschütteln mit Wasser entfernt, die     Ben-          zollösung    nach dem Trocknen verdampft und  der Rückstand im Hochvakuum destilliert.

    Man erhält so in guter Ausbeute das N-(2-           Phenoxy-        äthyl-1)    - N-     methyl-        2',5'-dimethyl-          pyrrolidino-acetamid,    welches ein unter 0,08 mm  bei 150-151  siedendes farbloses Öl darstellt.  



  Die Reaktion kann auch ohne V     erdün-          nungs-    und Kondensationsmittel durchgeführt  werden, indem man beispielsweise das N-(2  Phenoxy-äthyl-1)-N-methylamin mit     2,5-Di-          methyl-pyrrolidino    -     essigsäurechlorid-        hydro-          chlorid    trocken erhitzt, anschliessend die Re  aktionsmasse mit Wasser verdünnt und in  üblicher Weise aufarbeitet.



  Process for the production of a new basic substituted fatty acid amide. The subject of the present patent is a process for the preparation of a new basic substituted fatty acid amide, wel Ches is characterized in that one is based on a compound of the formula
EMI0001.0004
    a compound of the formula
EMI0001.0005
    in which formulas X and Y are reactive. residues that are split off during the reaction can act.



  Compounds of the formula I that can be used for conversion are, for example: The free amine (Y = H), but also its salts, such as, for example, the hydrochloride or the sulfate.



  Examples of possible compounds of the formula II are: 2,5-dimethyl-pyrrolidino-acetic acid itself and its reactive functional derivatives such as its halides, their esters, their anhydrides, for example the pure and mixed ones i Anhydrides with phosphoric acid, sulfuric acid and carbonic acid etc.



  You can, for example, N- (2-phenoxy-ethyl-1) -N-methylamine or a salt of the same in the presence of a dehydrating agent suitable for this purpose such as phosphorus pentoxide, phosphorus oxychloride, etc. with 2,5-dimethylpyrrolidinoacetic acid act.



  You can also use N- (2-phenoxy-ethyl-1) -N-methylamine or a salt thereof ben with a 2,5-dimethylamine-pyrrolidino-acetic acid halide (or a salt of such) or an anhydride Bring reaction.



  It is also possible to acylate N- (2-phenoxy-ethyl-1) -N-methylamine with a 2,5-dimethyl-pyrrolidino-acetic acid ester, preferably an aryl ester, at an elevated temperature.



  The N- (2-phenoxy-ethyl-1) -N-methyl-2 ', 5'-dimethyl-pyrrolidino-acetamide obtained in this way forms a colorless oil which boils below 0.08 mm at 150-151 .



  The new amide is to be used as a local anesthetic and as an intermediate for the production of further derivatives.



  <I> Example: </I> 15.2 g of N- (2-phenoxy-ethyl-1) -N-methylamine in benzene are mixed with a mixture of 20 g of 2,5-dimethyl-pyrrolidino-acetic acid chloride hydrochloride and heated 20 parts by weight of triethylamine. The triethylamine hydrochloride formed is then removed by shaking with water, the benzene solution is evaporated after drying and the residue is distilled in a high vacuum.

    The N- (2-phenoxyethyl-1) -N-methyl-2 ', 5'-dimethylpyrrolidino-acetamide, which is a colorless oil boiling below 0.08 mm at 150-151, is obtained in good yield .



  The reaction can also be carried out without a diluent and condensation agent, for example by drying the N- (2-phenoxy-ethyl-1) -N-methylamine with 2,5-dimethyl-pyrrolidino-acetic acid chloride hydrochloride heated, then the Re action mass diluted with water and worked up in the usual way.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, da durch gekennzeichnet, dass man auf eine Ver bindung der Formel EMI0002.0014 eine Verbindung der Formel EMI0002.0015 in welchen Formeln X und Y reaktionsfähige, bei der Reaktion sich abspaltende Reste be deuten, einwirken lä.sst. Das auf diese Weise erhaltene N-(2-Phen- oxy-äthyl-1) - N - methyl - 2',5' - dimethyl - pyr ro- lidino-a.cetamid ist ein farbloses, unter 0,08 mm bei 150-151 siedendes Öl. <B> PATENT CLAIM: </B> Process for the preparation of a new basic substituted fatty acid amide, characterized in that one is based on a compound of the formula EMI0002.0014 a compound of the formula EMI0002.0015 in which formulas X and Y are reactive residues that are split off during the reaction. The N- (2-phenoxy-ethyl-1) - N - methyl - 2 ', 5' - dimethyl - pyrrolidino-a.cetamide obtained in this way is colorless, less than 0.08 mm at 150 -151 boiling oil. Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man N-(2-Phenoxy-äthyl- 1) -N-methylamin mit einem 2,5-Dimethyl- pyrrolidino-essigsäurehalogenid umsetzt. The new amide will be used as a local anesthetic and as an intermediate product. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that N- (2-phenoxy-ethyl-1) -N-methylamine is reacted with a 2,5-dimethylpyrrolidino-acetic acid halide.
CH311563D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311563A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311563T 1952-06-08
CH306201T 1955-03-31

Publications (1)

Publication Number Publication Date
CH311563A true CH311563A (en) 1955-11-30

Family

ID=25735090

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311563D CH311563A (en) 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide.

Country Status (1)

Country Link
CH (1) CH311563A (en)

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