CH311694A - 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
CH311694A
CH311694A CH311694DA CH311694A CH 311694 A CH311694 A CH 311694A CH 311694D A CH311694D A CH 311694DA CH 311694 A CH311694 A CH 311694A
Authority
CH
Switzerland
Prior art keywords
fatty acid
acid amide
substituted fatty
production
methyl
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 CH311694A publication Critical patent/CH311694A/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
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • 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
    • 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

Landscapes

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

Description

  

  Verfahren zur Herstellung eines neuen basisch     substituierten        Fettsäureamides.       Gegenstand des vorliegenden Patentes bil  det. ein Verfahren     zur    Herstellung eines neuen  basisch     substituierten        Fettsäureamides,    wel  ches dadurch gekennzeichnet ist, dass man eine  Verbindung der Formel  
EMI0001.0006     
    in welcher X einen reaktionsfähigen, während  der Reaktion sieh abspaltenden Rest bedeutet,  mit.     2-Methyl-piperidin        umsetzt..     



  Der Rest. X kann in einem Halogenatom  oder einem sonstigen für den Austausch gegen  den basischen Rest, geeigneten reaktionsfähi  gen     Substituenten,    wie z. B. einer     Alky1sul-          fonyioxy-    oder     Arylsulfonyloxygruppe,    beste  hen. Der     Anstaiusch    der Gruppe X gegen den       2-llethyl-pipericlinrest    erfolgt z. B. durch ein  faehes     Erwärmen    mit     2-LNletbyl-piperidin,    ge  gebenenfalls in Gegenwart eines basisch     re-          agierenden    Kondensationsmittels oder von 2  Met.hyl-piperidin im Überschuss.

   Das     N-(2-          Phenoxyäthyl-1)-N-        methyl-        2'-methyl-piperi-          clinoaceta.mid    ist ein farbloses, unter 0,06 mm  bei 153-154  siedendes Öl.  



  Das neue     Amid    soll als Lokalanästhetikum  und als Zwischenprodukt zur Herstellung wei  terer Derivate Verwendung finden.    <I>Beispiel:</I>  22,8 g     N-(2-Phenoxyäthyl-1)-N-methyl-          ehloracetamid    und 19,9g     2-Methyl-pipericlin     werden     zusammen    in 150     cm?,        abs.    Benzol 3    Stunden auf dem Wasserbad erhitzt. Das     Re-          aktionsgemisch    wird mit Wasser ausgeschüt  telt und dann mit.     2n-Salzsäure    ausgezogen.

    Darauf wird der salzsaure     Auszug    mit Äther  extrahiert, unter     Eiskühlung    mit     konz.    Na  tronlauge versetzt und das ausgeschiedene Öl  in Äther aufgenommen. Nach dem Trocknen  der Ätherauszüge über     Pottasche    wird der  Äther verdampft und der Rückstand im Hoch  vakuum     destilliert.     



  Dabei gewinnt man das unter 0,06 mm bei  153-154  siedende     N-(2-Phenoxyäthyl-1)-N-          methyl-2'-methyl-piperidinoaeetamid    in einer  Ausbeute von     601/o    der Theorie. Farbloses Öl,  schwer löslich in     Wasser,        gut    in organischen  Lösungsmitteln und in verdünnten Mineral  säuren.



  Process for the production of a new basic substituted fatty acid amide. Subject of the present patent bil det. a process for the preparation of a new basic substituted fatty acid amide, wel Ches is characterized in that a compound of the formula
EMI0001.0006
    in which X denotes a reactive radical which is split off during the reaction, with. 2-methyl-piperidine converts.



  The radical. X can be in a halogen atom or another for the exchange against the basic radical, suitable reactive conditions substituents such. B. an alky1sulfonyioxy or arylsulfonyloxy group, best hen. The group X against the 2-llethyl-pipericlinrest is added, for. B. by a faehes heating with 2-Lletbyl-piperidine, if necessary in the presence of a basic reacting condensing agent or 2 Met.hyl-piperidine in excess.

   The N- (2-phenoxyethyl-1) -N-methyl-2'-methyl-pipericlinoaceta.mid is a colorless oil, boiling below 0.06 mm at 153-154.



  The new amide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. <I> Example: </I> 22.8 g of N- (2-phenoxyethyl-1) -N-methyl-ehloracetamide and 19.9 g of 2-methyl-pipericline are mixed together in 150 cm ?, abs. Benzene heated on a water bath for 3 hours. The reaction mixture is shaken out with water and then with. 2N hydrochloric acid extracted.

    The hydrochloric acid extract is then extracted with ether, with conc. Sodium hydroxide solution was added and the oil which had separated out 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-phenoxyethyl-1) -N-methyl-2'-methyl-piperidinoaetamide boiling below 0.06 mm at 153-154 is obtained in a yield of 601 / o of theory. Colorless oil, sparingly soluble in water, good in organic solvents and in dilute mineral acids.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, da durch gekennzeichnet, dass man eine Verbin dung der Formel EMI0001.0048 in welcher X einen reaktionsfähigen, während der Reaktion sieh abspaltenden Rest bedeutet, mit 2-Methyl-piperidin umsetzt. Das auf diese Weise erhaltene N-(2-Phenoxyäthyl-1)-N-me- thyi-2'-methyl-piperidinoaeetamid bildet ein farbloses, unter 0,06 mm bei 153-154 sieden des 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 EMI0001.0048 in which X denotes a reactive radical which is split off during the reaction, with 2-methylpiperidine. The N- (2-phenoxyethyl-1) -N-methyi-2'-methyl-piperidinoaetamide obtained in this way forms a colorless oil, boiling below 0.06 mm at 153-154. Das neue Amid soll als Lokalanästhetikum und als Zwisehenprodukt Verwendung finden. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein N-(2-Phenoxy- äthyl-1)-N-methyl-halo-enaeetamid mit 2-1Ie- thyl-piperidin reagieren lässt. The new amide is to be used as a local anesthetic and as an intermediate product. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that an N- (2-phenoxy-ethyl-1) -N-methyl-halo-enaetamide is allowed to react with 2-1-ethyl-piperidine.
CH311694D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311694A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311694T 1952-06-08
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311694A true CH311694A (en) 1955-11-30

Family

ID=25735427

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311694D CH311694A (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) CH311694A (en)

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