CH311562A - 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
CH311562A
CH311562A CH311562DA CH311562A CH 311562 A CH311562 A CH 311562A CH 311562D A CH311562D A CH 311562DA CH 311562 A CH311562 A CH 311562A
Authority
CH
Switzerland
Prior art keywords
fatty acid
production
acid amide
substituted fatty
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 CH311562A publication Critical patent/CH311562A/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)
  • Hydrogenated Pyridines (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  
EMI0001.0008     
    eine Verbindung der Formel  
EMI0001.0009     
    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 Hydrochlorid  oder das Sulfat.  



  Als Verbindungen der     Formel        II    kommen  beispielsweise in Frage:     2,6-Dimethyl-piperi-          dino-essigsäure    selbst und ihre reaktionsfähi  gen funktionellen Derivate wie ihre     Haloge-          nide,    ihre Ester, ihre     Anhydride,    beispiels  weise die reinen und auch die gemischten       Anhydride    mit Phosphorsäure, Schwefelsäure  und     Kohlensäure        usf.     



  Man kann     beispielsweise        N-(2-Phenoxy-          äthyl-1)-N-methyl-amin    oder auch ein     Salz     desselben in Gegenwart eines für diese Zwecke    geeigneten wasserabspaltenden     Mittels    wie       Phosphorpentoxyd,        Phosphoroxychlorid        usf.     mit     2,6-Dimethyl-piperidino-essigsäure    behan  deln.  



  Weiter kann man auch     N-(2-Phenoxy-          äthyl-1)-N-methyl-amin    bzw. ein Salz dessel  ben mit einem     2,6-Dimethyl-piperidino-essig-          säurehalogenid    (bzw. einem     Salz    eines sol  chen) oder einem     Anhydrid    zur Reaktion  bringen.  



  Es ist weiterhin auch möglich,     N-(2-Phen-          oxy-äthyl-1)-N-methyl-amin        mit    einem     2,6-Di-          methyl    -     piperidino    -     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',6'-     dimethyl-        piperi-          dino-acetamid    bildet ein farbloses, unter  0,06 mm bei 157-158  siedendes öl.  



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



  <I>Beispiel:</I>  15,2g     N-(2-Phenoxy-äthyl-1)-N-methyl-          amin    in Benzol werden     mit    einer Mischung  von 22,6 g     2,6-Dimethyl-piperidino-essigsäure-          chlorid-hydrochlorid    und 20 g     Triäthylamin     erwärmt.

   Anschliessend wird das gebildete       Triäthylaminhydrochlorid    durch     Ausschütteln     mit Wasser entfernt, die     Benzollösung    nach  dem Trocknen     verdampft        und    der     Rückstand     im     IIochvakuum        destilliert.    Man erhält so in       guter    Ausbeute das N-(2-Phenoxy-äthyl-1)-N-           methyl-2',6'-dimethyl-piperidino-acetamid,    wel  ches ein unter 0,06 mm bei 157-158  sieden  des farbloses Öl darstellt.  



  Die Reaktion kann auch ohne     Verdün-          nungs-    und Kondensationsmittel durchgeführt  werden, indem man beispielsweise das N-(2  Phenoxy-äthyl-1)-N-methyl-amin mit     2,6-Di-          inethyl-piperidino-essigsäure    -     chlorid-hydro-          ehlorid    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
EMI0001.0008
    a compound of the formula
EMI0001.0009
    in which formulas X and Y are reactive residues that are split off during the reaction.



  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 the hydrochloride or the sulfate, for example.



  Examples of possible compounds of the formula II are: 2,6-dimethyl-piperidino-acetic acid itself and its reactive functional derivatives such as its halides, its esters, their anhydrides, for example the pure and also the mixed anhydrides Phosphoric acid, sulfuric acid and carbonic acid etc.



  For example, N- (2-phenoxyethyl-1) -N-methyl-amine or a salt thereof in the presence of a dehydrating agent suitable for this purpose such as phosphorus pentoxide, phosphorus oxychloride, etc. with 2,6-dimethylpiperidinoacetic acid to treat.



  You can also use N- (2-phenoxy-ethyl-1) -N-methyl-amine or a salt thereof with a 2,6-dimethyl-piperidino-acetic acid halide (or a salt of such) or bring an anhydride to reaction.



  It is also possible to acylate N- (2-phenoxy-ethyl-1) -N-methyl-amine with a 2,6-dimethyl - piperidino - acetic acid ester, preferably an aryl ester, at an elevated temperature .



  The N- (2-phenoxy-ethyl-1) -N-methyl-2 ', 6'-dimethylpiperidino-acetamide obtained in this way forms a colorless one, boiling below 0.06 mm at 157-158 oil.



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



  <I> Example: </I> 15.2 g of N- (2-phenoxy-ethyl-1) -N-methyl-amine in benzene are mixed with a mixture of 22.6 g of 2,6-dimethyl-piperidino-acetic acid chloride hydrochloride and 20 g of triethylamine heated.

   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-phenoxy-ethyl-1) -N-methyl-2 ', 6'-dimethyl-piperidino-acetamide, which boils below 0.06 mm at 157-158 of the colorless, is obtained in good yield Represents oil.



  The reaction can also be carried out without diluents and condensation agents, for example by adding the N- (2-phenoxy-ethyl-1) -N-methyl-amine with 2,6-dimethyl-piperidino-acetic acid - chloride-hydro - Ehlorid heated dry, then the Re action mass diluted with water and worked up in the usual way.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, da durch gekennzeichnet, dass man auf eine Ver bindung der Formel EMI0002.0009 eine Verbindung der Formel EMI0002.0011 in welchen Formeln X und Y reaktionsfähige, bei der Reaktion sich abspaltende Reste be deuten, einwirken lässt. PATENT CLAIM: Process for the production of a new basic substituted fatty acid amide, characterized in that one is linked to a compound of the formula EMI0002.0009 a compound of the formula EMI0002.0011 in which formulas X and Y are reactive residues that are split off during the reaction. Das auf diese Weise erhaltene N-(2-Phen- oxy-äthyl-1)-N-methy l- 2',6'- dimethyl-piperi- dino-acetamid ist ein farbloses, unter 0,06 mm bei 157-158 siedendes Öl: Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. UNTER-ANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man N-(2-Phenoxy-äthyl- 1)-N-methyl-amin mit einem 2,6-Dimethyl- piperidino-essigsäure-halogenid umsetzt. The N- (2-phenoxy-ethyl-1) -N-methyl-2 ', 6'-dimethyl-piperidino-acetamide obtained in this way is colorless, less than 0.06 mm at 157-158 Boiling oil: The new amide will be used as a local anesthetic and as an intermediate product. SUB-CLAIM: Process according to patent claim, characterized in that N- (2-phenoxy-ethyl-1) -N-methyl-amine is reacted with a 2,6-dimethyl-piperidino-acetic acid halide.
CH311562D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311562A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311562T 1952-06-08
CH306201T 1955-03-31

Publications (1)

Publication Number Publication Date
CH311562A true CH311562A (en) 1955-11-30

Family

ID=25735089

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311562D CH311562A (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) CH311562A (en)

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