CH311565A - 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
CH311565A
CH311565A CH311565DA CH311565A CH 311565 A CH311565 A CH 311565A CH 311565D A CH311565D A CH 311565DA CH 311565 A CH311565 A CH 311565A
Authority
CH
Switzerland
Prior art keywords
production
fatty acid
methyl
acid amide
piperidino
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 CH311565A publication Critical patent/CH311565A/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

  

  <B>Verfahren zur Herstellung</B>     eines   <B>neuen basisch substituierten</B>     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 1 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-Methyl-piperidino-          cssibsäure    selbst und ihre reaktionsfähigen       funktionellen    Derivate wie ihre     Halogenide,     ihre Ester, ihre     Anhydride,    beispielsweise die  reinen und auch die gemischten     Anhydride     mit Phosphorsäure,     Sehwefelsäure    und Koh  lensäure     usf.     



  Man kann beispielsweise     N-(2-Phenoxy-          ät.lryl-1)-N-methylamin    oder auch ein Salz des  selben in Gegenwart eines für diese Zwecke  geeigneten wasserabspaltenden Mittels     wie            Phosphorpentoxyd,        Phosphoroxychlorid        usf.     mit     2-Methyl-piperidino-essigsäure    behandeln.  



  Weiter     kann    man auch     N-(2-Phenoxy-          äthyl-1)-N-methylamin    bzw. ein Salz dessel  ben mit einem     2-Methyl-piperidino-essigsäure-          halogenid    (bzw. einem Salz eines solchen)  oder einem     Anhydrid    zur Reaktion bringen.  



  Es ist weiterhin auch möglich,     NT-(2-Phen-          oxy-äthyl-1)-N-methylamin    mit einem     2-Me-          thyl-piperidino-essigsäureester,    vorzugsweise  einem     Arylester,    bei erhöhter Temperatur zu       aeylieren.     



  Das auf diese Weise erhaltene     N-(2-Phen-          oxy-äthyl-1)    -N -     methyl    - 2' -     methyl    -     piperidino-          acetamid    bildet ein farbloses, ' unter 0,06 mm  bei     153-l.54     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-ätlryl-1)-N-met.hyl-          amin    in Benzol werden mit einer Mischung  von 20 g     2-Methyl-piperidino-essigsäurechlo-          rid-hydrochlorid    und 20 g     Triäthylamin    er  wärmt. Anschliessend wird das gebildete     Tri-          äthylarninhydrochlorid    durch Ausschütteln  mit Wasser entfernt, die     Benzollösrnmg    nach       clern    Trocknen. verdampft und der     Rüekstand     im Hochvakuum destilliert.

   Man erhält so in  guter     Ausbeute    das     N-(2-Phenoxy-äthyl-1)-N-          methyl-2'-methyl-piperidino-acetamid,    welches  ein unter 0,06 mm bei 153-154  siedendes  farbloses Öl darstellt.      Die Reaktion kann auch ohne     Verdün-          nungs-    und     Kondensationsmittel    durchgeführt  werden, indem man beispielsweise das     N-(2-          Phenoxy-äthyl-1)        -N-methylamin    mit     2-Me-          thyl.-pip        eridino-essigsäurechlorid-hydrochlor        id     trocken erhitzt,

   anschliessend die Reaktions  masse mit Wasser verdünnt und in üblicher  Weise aufarbeitet.



  <B> Process for the production </B> of a <B> new basic substituted </B> 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 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.



  Compounds of the formula 1 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-methyl-piperidino-cssibic 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 carbonic acid, etc.



  For example, N- (2-phenoxy- ät.lryl-1) -N-methylamine or a salt of the same can be treated with 2-methyl-piperidino-acetic acid in the presence of a dehydrating agent suitable for this purpose, such as phosphorus pentoxide, phosphorus oxychloride, etc. .



  N- (2-phenoxyethyl-1) -N-methylamine or a salt thereof can also be reacted with a 2-methyl-piperidino-acetic acid halide (or a salt of such) or an anhydride .



  It is furthermore also possible to aeylate NT- (2-phenoxy-ethyl-1) -N-methylamine with a 2-methylpiperidino-acetic acid ester, preferably an aryl ester, at elevated temperature.



  The N- (2-phenoxy-ethyl-1) -N-methyl-2'-methyl-piperidino-acetamide obtained in this way forms a colorless oil which boils below 0.06 mm at 153-1.54.



  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-ätlryl-1) -N-meth.hyl- amine in benzene are mixed with a mixture of 20 g of 2-methyl-piperidino-acetic acid chloride hydrochloride and 20 g of triethylamine it warms. The triethylamine hydrochloride formed is then removed by shaking with water, and the benzene solution is removed after drying. evaporated and the residue distilled in a high vacuum.

   The N- (2-phenoxy-ethyl-1) -N-methyl-2'-methyl-piperidino-acetamide, which is a colorless oil boiling below 0.06 mm at 153-154, is thus obtained in good yield. The reaction can also be carried out without a diluent or condensation agent, for example by heating the N- (2-phenoxy-ethyl-1) -N-methylamine dry with 2-methyl-piperidino-acetic acid chloride hydrochloride ,

   then the reaction mass is 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 EMI0002.0013 eine Verbindung der Formel EMI0002.0014 in welehen Formeln X und Y reaktionsfähige, bei der Reaktion sieh abspaltende Reste be deuten, einwirken lä.sst. Das auf diese Weise erhaltene N-(2-Phen oxy-äthyl-1)-N-methyl-2'-methyl-piperidino- acetamid ist ein farbloses, unter 0,06 mm bei 153-1.54 siedendes Öl. 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 EMI0002.0013 a compound of the formula EMI0002.0014 in which formulas X and Y are reactive residues that split off during the reaction. The N- (2-phenoxy-ethyl-1) -N-methyl-2'-methyl-piperidino-acetamide obtained in this way is a colorless oil boiling below 0.06 mm at 153-1.54. Das neue Amid soll als Lokalanästhetikum und als Zwisehenprodukt Verwendung finden. UNTERANSPRUCH Verfahren naeh Patentanspruch, dadureh gekennzeichnet, dass man N - (2 - Phenoxy- äthyl-1)-N-methylamin mit einem 2-:4lethy1- piperidino-essigsäurehalogenid umsetzt. The new amide is to be used as a local anesthetic and as an intermediate product. SUBCLAIM A method according to the patent claim, characterized in that N - (2 - phenoxyethyl-1) -N-methylamine is reacted with a 2-: 4lethy1- piperidino-acetic acid halide.
CH311565D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311565A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311565T 1952-06-08
CH306201T 1955-03-31

Publications (1)

Publication Number Publication Date
CH311565A true CH311565A (en) 1955-11-30

Family

ID=25735092

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311565D CH311565A (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) CH311565A (en)

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