CH311683A - 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
CH311683A
CH311683A CH311683DA CH311683A CH 311683 A CH311683 A CH 311683A CH 311683D A CH311683D A CH 311683DA CH 311683 A CH311683 A CH 311683A
Authority
CH
Switzerland
Prior art keywords
amide
fatty acid
substituted fatty
production
acid amide
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 CH311683A publication Critical patent/CH311683A/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,     da.ss    man eine  Verbindung der Formel  
EMI0001.0006     
    in welcher X einen reaktionsfähigen, während  der Reaktion sich abspaltenden Rest bedeutet,  mit     2-:4lethyl-piperidin    umsetzt..  



  Der Rest. X kann in einem     Halogenatom     oder einem sonstigen für den Austausch gegen  den     basisehen    Rest geeigneten reaktionsfähi  gen     Substituenten,    wie z. B. einer     Alkylsul-          fonyloxy-    oder     Arylsulfonyloxygruppe,        beste-          lien.Der    Austausch der Gruppe X gegen den       ?-Methy        1-piperidinorest        erfolgt    z.

   B. durch ein  faches Erwärmen mit     2-hlethyl-piperidi.n,    ge  gebenenfalls in     Gegenwart    eines basisch reagie  renden     Kondensationsmittels    oder von     2-Me-          tliyl-piperidin    im     I"berschuss.    Das     a-llethyl-          piperidino-essigsäure-N-        (3-phenoxy-propyl-2)        -          amid    ist ein farbloses, unter 0,02 mm bei 1.46  bis     1.17     siedendes Öl.  



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



       Beispiel:     18,4 g     Chloressigsäure-l@T-(3-phenoxy-pro-          p@-1-2)-amid    und 1.6,0 g     2-Methyl-piperidin       werden zusammen in 150     eins        abs.    Benzol 5  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 0,02 mm bei  146-147  siedende     a.-Methyl-piperidino-essig-          säure-N-(3-phenoxy-propyl-2)-amid    in einer       Ausbeute        von        60,5%        der        Theorie.        Farbloses     Öl, schwer löslich in Wasser, gut in organi  schen Lösungsmitteln und in verdünnten Mi  neralsäuren.



  Process for the production of a new basic substituted fatty acid amide. The subject 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 is used
EMI0001.0006
    in which X denotes a reactive radical which is split off during the reaction, with 2-: 4lethyl-piperidine.



  The radical. X can be in a halogen atom or other reactive substituents suitable for replacement with the basic radical, such as. B. an alkylsulphonyloxy or arylsulphonyloxy group, best lien. The exchange of the group X for the? -Methy 1-piperidino radical takes place z.

   B. by simple heating with 2-methyl-piperidino, if necessary in the presence of a basic reacting condensing agent or 2-methyl-piperidine in excess. 3-phenoxy-propyl-2) - amide is a colorless oil that boils below 0.02 mm at 1.46 to 1.17.



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



       Example: 18.4 g of chloroacetic acid-l @ T- (3-phenoxy-prop @ -1-2) -amide and 1.6.0 g of 2-methyl-piperidine are mixed together in 150 abs. Benzene heated on a water bath for 5 hours. The reaction mixture is extracted with water and then extracted with 2N hydrochloric acid. The hydrochloric acid extract is then extracted with ether, with conc. Sodium hydroxide solution added. and the excreted oil is absorbed into ether.

   After the ether extracts have dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.



  The α-methyl-piperidino-acetic acid-N- (3-phenoxy-propyl-2) -amide, boiling below 0.02 mm at 146-147, is obtained in a yield of 60.5% 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 EMI0001.0055 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit 2-Methyl-piperidin umsetzt. Das auf diese Weise erhaltene a-Methyl-piperidino-.essig- säure-N-(3-phenohy-propy1-2)-amid bildet ein farbloses, unter 0,02 mm bei 146-147 sie dendes 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 EMI0001.0055 in which X is a reactive radical which is split off during the reaction, is reacted with 2-methylpiperidine. The α-methyl-piperidino-acetic acid-N- (3-phenohy-propy1-2) -amide obtained in this way forms a colorless oil which sinks below 0.02 mm at 146-147. Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadureh gekennzeiehnet, dass man ein Halogenessig- säure-N-(3-phenosy-propz-l-2)-amid mit 2-Me- thyl-piperidin reagieren lässt. The new amide will be used as a local anesthetic and as an intermediate product. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that a haloacetic acid-N- (3-phenosy-propz-l-2) -amide is allowed to react with 2-methylpiperidine.
CH311683D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311683A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311683T 1952-06-08
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311683A true CH311683A (en) 1955-11-30

Family

ID=25735416

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311683D CH311683A (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) CH311683A (en)

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