CH311557A - 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
CH311557A
CH311557A CH311557DA CH311557A CH 311557 A CH311557 A CH 311557A CH 311557D A CH311557D A CH 311557DA CH 311557 A CH311557 A CH 311557A
Authority
CH
Switzerland
Prior art keywords
fatty acid
substituted fatty
production
acid amide
ethyl
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 CH311557A publication Critical patent/CH311557A/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 netten  basisch substituierten     Fettsäureamides,        wel-          elies        dadureh    gekennzeichnet 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     T    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 11 kommen  beispielsweise in Frage:     2-Methyl-piperidino-          essigsäure    selbst und ihre reaktionsfähigen  funktionellen Derivate wie ihre     Halogenide,     ihre Ester, ihre     Anhydride,    beispielsweise die  reinen und auch die gemischten     Anhydride     mit Phosphorsäure,     Schwefelsäure    und Koh  lensäure     usf.     



  Man kann beispielsweise     N-[2-(2',4',6'-Tri-          metliyl-phenoxy)-äthyl-1]-methylamin    oder    auch ein Salz desselben in Gegenwart eines  für diese Zwecke geeigneten wasserabspalten  den Mittels wie     Phosphorpentoxyd,    Phosphor  oxyehlorid     usf.    mit     2-Methyl-piperidinoessig-          säure    behandeln.  



  Weiter     kann    man auch     N-[2-(2',4',6'-Tri-          methyl    -     phenoxy)    -     äthyl    -1 ] -     methylamin    bzw.  ein Salz desselben mit einem     2-Methyl-piperi-          dinoessigsäitrehalogenid    (bzw. einem Salz  eines solchen) oder einem     Anhydrid    zur Re  aktion bringen.  



  Es ist weiterhin auch möglich, N-[2-(2',4',       6'-        Trimethyl    -     phenoxy)        -äthyl-1    ]     -methylamin     mit einem     2-Methyl-piperidinoessigsäureester,     vorzugsweise einem     Arylester,    bei erhöhter  Temperatur zu     acylieren.     



  Das auf diese Weise erhaltene     a-Methyl-          piperidinoessigsäure-N-    [2- (2',4',6'-     trimethyl-          phenoxy)-äthyl-1]-methylamid    bildet einfarb  loses, unter 0,02 mm bei 170-171  sieden  des öl.  



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



       Beispiel:   <I>-</I>  19,3 g     N-[2-(2',4',6'-Trimethyl-phenoxy)-          äthyl-1    ]     -methylamin    in Benzol werden mit  einer Mischung von 21,2 g     2-Methyl-piperi-          dinoessigsäurechlorid-hydrochlorid    und 20,2 g       Triäthylamin    erwärmt. Anschliessend wird  das gebildete     Triäthylaminhydrochlorid    durch  Ausschütteln mit Wasser entfernt, die Benzol  lösung nach dem Trocknen verdampft und      der Rückstand im Hochvakuum destilliert.

    Man erhält so in guter Ausbeute das     a-Me-          thyl    -     piperidinoessigsäure    -N - [2 -     (2',4',6'-tri-          methyl    -     phenoxy)    -     äthyl    -1 ] -     methylamid,    wel  ches ein unter 0,02 mm bei     170-171.     sieden  des farbloses Öl darstellt.  



  Die- Reaktion kann auch ohne     Verdün-          niuigs-und    Kondensationsmittel durchgeführt  werden, indem man beispielsweise das     2-Me-          thyl-piperidinoessigsäurechlorid-hydrochlorid     mit     N-[2-(2',4',6'-Trimethyl-phenoxy)-äthyl-          1]-methylamin    trocken erhitzt, anschliessend  die     Reaktionsmasse    mit Wasser verdünnt und  in üblicher Weise aufarbeitet.



  Process for the production of a new basic substituted fatty acid amide. The subject matter of the present patent is a process for the preparation of a nice, basic substituted fatty acid amide, which is characterized by the fact that a compound 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 the formula T which can be used for a conversion are, for example: The free amine (Y = H), but also its salts, such as the hydrochloride or the sulfate.



  Examples of possible compounds of formula 11 are: 2-methylpiperidinoacetic acid itself and its reactive functional derivatives such as its halides, its esters, its anhydrides, for example the pure and also the mixed anhydrides with phosphoric acid, sulfuric acid and carbon acid, etc.



  For example, N- [2- (2 ', 4', 6'-trimethyl-phenoxy) -ethyl-1] -methylamine or a salt thereof in the presence of a dehydrating agent suitable for this purpose such as phosphorus pentoxide, phosphorus Treat oxyehloride etc. with 2-methyl-piperidinoacetic acid.



  In addition, N- [2- (2 ', 4', 6'-trimethyl-phenoxy) -ethyl -1] -methylamine or a salt thereof with a 2-methyl-piperidinoacetic acid halide (or a Salt of such) or an anhydride to react.



  It is furthermore also possible to acylate N- [2- (2 ', 4', 6'-trimethyl-phenoxy) -ethyl-1] -methylamine with a 2-methylpiperidinoacetic acid ester, preferably an aryl ester, at elevated temperature.



  The a-methylpiperidinoacetic acid-N- [2- (2 ', 4', 6'-trimethylphenoxy) -ethyl-1] -methylamide obtained in this way forms a colorless, less than 0.02 mm at 170-171 boiling the oil.



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



       Example: <I> - </I> 19.3 g of N- [2- (2 ', 4', 6'-trimethyl-phenoxy) -ethyl-1] -methylamine in benzene are mixed with a mixture of 21.2 g of 2-methyl-piperidinoacetic acid chloride hydrochloride and 20.2 g of triethylamine were 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 α-methyl piperidinoacetic acid -N - [2 - (2 ', 4', 6'-trimethyl-phenoxy) -ethyl-1] -methylamide, which is one below 0, is obtained in good yield. 02 mm for 170-171. represents boiling of the colorless oil.



  The reaction can also be carried out without diluents and condensation agents, for example by converting the 2-methylpiperidinoacetic acid chloride hydrochloride with N- [2- (2 ', 4', 6'-trimethylphenoxy) ethyl - 1] -methylamine heated dry, then diluted the reaction mass 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 EMI0002.0019 eine Verbindung der Formel EMI0002.0020 in welchen Formeln X und Y reaktionsfähige, bei der Reaktion sich abspaltende Reste be deuten, einwirken lässt. Das auf diese Weise erhaltene a-Methyl- piperidinoessigsäure-N- [2- (2',4',6'-trimethyl- phenoxy)-ätliyl-1]-methylamid ist ein farb loses, unter 0,02 mm bei 170-171 sieden des Öl. PATENT CLAIM Process for the preparation of a new basic substituted fatty acid amide, characterized in that one is based on a compound of the formula EMI0002.0019 a compound of the formula EMI0002.0020 in which formulas X and Y are reactive residues that are split off during the reaction. The a-methylpiperidinoacetic acid-N- [2- (2 ', 4', 6'-trimethylphenoxy) -ethyl-1] -methylamide obtained in this way is a colorless, less than 0.02 mm at 170- 171 boiling the oil. Das neue Amid soll als Lokalanästhetikum und als Zwisebenprodukt Verwendung finden. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man N-[2-(2;4',6'-Tri- methyl - phenoxy) - äthyl -1 ] -methylamin mit einem 2-Methyl-piperidinoessigsäurehalogenid umsetzt. The new amide is said to be used as a local anesthetic and as an intermediate by-product. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that N- [2- (2; 4 ', 6'-trimethyl-phenoxy) -ethyl -1] -methylamine is reacted with a 2-methyl-piperidinoacetic acid halide.
CH311557D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311557A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311557T 1952-06-08
CH306201T 1955-03-31

Publications (1)

Publication Number Publication Date
CH311557A true CH311557A (en) 1955-11-30

Family

ID=25735084

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311557D CH311557A (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) CH311557A (en)

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