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CH311705A - 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
CH311705A
CH311705A CH311705DA CH311705A CH 311705 A CH311705 A CH 311705A CH 311705D A CH311705D A CH 311705DA CH 311705 A CH311705 A CH 311705A
Authority
CH
Switzerland
Prior art keywords
fatty acid
acid amide
production
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 CH311705A publication Critical patent/CH311705A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)

Description

  

  Verfahren     zur        Herstellung    eines neuen basisch substituierten     Fettsäureamides.            Clegenstand    des     vorliegenden    Patentes bil  det ein Verfahren zur Herstellung eines neuen  basisch substituierten     Fettsäureamides,        wel-          elies    dadurch gekennzeichnet ist, dass man eine  Verbindung der Formel  
EMI0001.0009     
         iii        weleher    X einen reaktionsfähigen, während  der Reaktion sich abspaltenden Rest bedeutet,  mit     2,6-Dimethylpiperidin    umsetzt.  



  Der Rest X kann in einem Halogenatom  oder einem sonstigen für den Austausch gegen  den basischen Rest geeigneten reaktionsfähigen       Substituenten,    wie z. B. einer     Alkylsülfonyl-          oxy-    oder     Arylsulfonyloxygriippe    bestehen.  Der Austausch der Gruppe X gegen den     2,6-          Dimethylpiperidinrest    erfolgt z. B. durch ein  faches Erwärmen mit     2,6-Dimethylpiperidin,          gegebenenfalls    in Gegenwart eines     basiseh     reagierenden Kondensationsmittels, oder von       ?,6-Dimethylpiperidin    im Überschuss.

   Das     N-          ('?-Phenoxy-äthyl-1)        -N-methy1-    2',6' -     dimethy        1-          pideridino-acetamid    ist ein farbloses, unter  0,06 mm bei 157-158  siedendes Öl. Das  neue     Amid    soll als Lokalanästhetikum und  als Zwischenprodukt zur Herstellung wei  terer Derivate Verwendung finden.  



       Beispiel:     22,8 g N     -(2-Phenoxy        -äthyl-1)-N-niethyl-          elilor-aeetamid    und 22,6 g 2,6-Dimethylpiperi-    dun werden zusammen in 150     cms        abs.    Benzol  6 Stunden auf dem Wasserbad erhitzt. Das  Reaktionsgemisch wird mit Wasser ausge  schüttelt und dann mit     2n-Salzsäure    ausge  zogen.

   Darauf wird der salzsaure Auszug mit  Äther extrahiert,     unter        Eiskühlung    mit     konz.     Natronlauge versetzt     und    das ausgeschiedene  Öl in Äther     aufgenommen.    Nach dem Trock  nen der Ätherauszüge über Pottasche wird der  Äther verdampft     und    der Rückstand im  Hochvakuum destilliert.  



  Dabei gewinnt man das unter 0,06 mm  bei 157-158  siedende     N-(2-Phenoxy-äthyl-1)-          N-methyl    -     2',6'-dimethylpiperidino-acetamid     als farbloses, säurelösliches Öl.



  Process for the production of a new basic substituted fatty acid amide. The status of the present patent forms a process for the preparation of a new basic substituted fatty acid amide, which is characterized in that a compound of the formula
EMI0001.0009
         iii which X means a reactive radical which is split off during the reaction, is reacted with 2,6-dimethylpiperidine.



  The radical X can be in a halogen atom or any other reactive substituent suitable for replacement with the basic radical, such as. B. an Alkylsulfonyl- oxy- or Arylsulfonyloxygriippe exist. The exchange of the group X against the 2,6-dimethylpiperidine radical takes place z. B. by a fold heating with 2,6-dimethylpiperidine, optionally in the presence of a basic reacting condensing agent, or?, 6-dimethylpiperidine in excess.

   The N- ('? -Phenoxy-ethyl-1) -N-methy1- 2', 6 '- dimethy 1-pideridino-acetamide is a colorless oil, boiling below 0.06 mm at 157-158. The new amide is to be used as a local anesthetic and as an intermediate for the production of further derivatives.



       Example: 22.8 g of N - (2-phenoxy-ethyl-1) -N-niethyl-elilor-aeetamide and 22.6 g of 2,6-dimethylpiperidune together in 150 cms of abs. Benzene heated on a water bath for 6 hours. The reaction mixture is shaken out with water and then extracted with 2N hydrochloric acid.

   The hydrochloric acid extract is then extracted with ether, with conc. Sodium hydroxide solution was added and the separated oil was taken up in ether. After the ether extracts have dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.



  The N- (2-phenoxy-ethyl-1) -N-methyl-2 ', 6'-dimethylpiperidino-acetamide, boiling below 0.06 mm at 157-158, is obtained as a colorless, acid-soluble oil.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, da durch gekennzeichnet, dass man eine Verbin dung der Formel EMI0001.0047 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit 2,6-Dimethylpiperidin umsetzt. Das auf diese Weise erhaltene N-(2-Phenoxy-äthyl-1)- N-methyl- 2',6'- dimethylpiperidino-acetamid bildet ein farbloses, unter 0,06 mm bei 157 bis 1.58 siedendes Öl. PATENT CLAIM: Process for the preparation of a new basic substituted fatty acid amide, characterized in that one is a compound of the formula EMI0001.0047 in which X denotes a reactive radical which is split off during the reaction, with 2,6-dimethylpiperidine. The N- (2-phenoxy-ethyl-1) -N-methyl-2 ', 6'-dimethylpiperidino-acetamide obtained in this way forms a colorless oil which boils below 0.06 mm at 157 to 1.58. Das neue Amid soll als Lokalanästhetikum und als Zwisehenprodukt Verwendung finden. UNTERANSPRUCH: Verfahren naeh Patentanspruch, dadurch gekennzeichnet, dass man ein N-(2-Phenoxy- äthyl-1)-N-methyl-halogenoacetamid mit 2,6- Dimethylpiperidin reagieren lässt. The new amide is to be used as a local anesthetic and as an intermediate product. SUBClaim: Method according to patent claim, characterized in that an N- (2-phenoxy-ethyl-1) -N-methyl-halogenoacetamide is allowed to react with 2,6-dimethylpiperidine.
CH311705D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311705A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311705T 1952-06-08
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311705A true CH311705A (en) 1955-11-30

Family

ID=25735438

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311705D CH311705A (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) CH311705A (en)

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