CH311665A - 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
CH311665A
CH311665A CH311665DA CH311665A CH 311665 A CH311665 A CH 311665A CH 311665D A CH311665D A CH 311665DA CH 311665 A CH311665 A CH 311665A
Authority
CH
Switzerland
Prior art keywords
sep
fatty acid
acid amide
production
substituted fatty
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 CH311665A publication Critical patent/CH311665A/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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines neuen basisch     substituierten        Fettsäureamides.       Gegenstand des vorliegenden Patentes bil  det ein Verfahren zur     Herstellung    eines neuen  basisch substituierten     Pettsäureamides,        wel-          ehes    dadurch gekennzeichnet ist, dass man  eine Verbindung der Formel  
EMI0001.0007     
    in     welcher    X einen reaktionsfähigen, während       cler    Reaktion sich abspaltenden Rest bedeutet,  mit     Diäthylamin    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-          fonyloxy-    oder     Arylslllfonyloxygruppe,    be  stehen. Der Austausch der Gruppe X gegen  den     Diäthylaminorest    erfolgt zum Beispiel  durch einfaches Erwärmen mit     Diäthylamin,          negebenenfalls    in Gegenwart eines basisch  reagierenden Kondensationsmittels oder von       Diäthylamin    im Überschuss.

   Das     Diäthyl-          a.minoessigsällre-N-        (3-o-chlor-phenoxy-propyl-          2)-metllplamid    ist ein farbloses, unter 0,08 mm  bei     l.60-162     siedendes Öl.  



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



  <I>Beispiel:</I>  27,6 g Chloressigsäure     -N-(3-o-chlor-phen-          oxy-propyl-2)-methylamid    und 15,5g Diäthyl-         amin    werden zusammen in 200     cm3        abs.    Ben  zol 3     Stunden    auf dem Wasserbad erhitzt.  Das Reaktionsgemisch wird mit Wasser aus  geschüttet und dann mit     2n-Salzsäure    aus  gezogen. Darauf     wird    der salzsaure Auszug  mit Äther extrahiert, unter Eiskühlung mit       konz.    Natronlauge versetzt und das ausge  schiedene Öl in Äther aufgenommen.

   Nach  dem Trocknen der Ätherauszüge über Pott  asche wird der Äther verdampft und der  Rückstand im     Hochvakuum    destilliert.  



  Dabei gewinnt man das unter 0.08 mm bei  160-162  siedende     Diäthylaminoessigsäure-N-          (3-o-chlor-phenoxy-propyl-2)-methylamid    in       einer        Ausbeute        von        60%        der        Theorie.        Farb-          loses    Öl,     schwer    löslich in Wasser, gut in  organischen     Lösungsmitteln    und in     verdiinn-          ten    Mineralsäuren.



  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
EMI0001.0007
    in which X denotes a reactive radical which is split off during the reaction, with diethylamine.



  The radical. X can be in a halogen atom or any other suitable reactive substituents for replacement with the basic radical, such as. B. an Alky1sulfonyloxy- or Arylslllfonyloxygruppe be. Group X is exchanged for the diethylamino radical, for example, by simply heating with diethylamine, possibly in the presence of a basic condensing agent or excess diethylamine.

   The diethyl a.minoessigsallre-N- (3-o-chloro-phenoxy-propyl-2) -metllplamid is a colorless oil that boils below 0.08 mm at 1.60-162.



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



  <I> Example: </I> 27.6 g of chloroacetic acid -N- (3-o-chloro-phenoxy-propyl-2) -methylamide and 15.5 g of diethylamine are mixed together in 200 cm3 of abs. Ben zol heated on a water bath for 3 hours. The reaction mixture is poured out with water and then drawn off with 2N hydrochloric acid. The hydrochloric acid extract is then extracted with ether, with conc. Sodium hydroxide was added and the separated oil was added to ether.

   After drying the ether extracts over pot ash, the ether is evaporated and the residue is distilled in a high vacuum.



  The diethylaminoacetic acid-N- (3-o-chloro-phenoxy-propyl-2) -methylamide boiling below 0.08 mm at 160-162 is obtained in a yield of 60% of theory. Colorless oil, sparingly soluble in water, good in organic solvents and in diluted mineral acids.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, da durch gekennzeichnet, dass man eine Verbin dung der Formel EMI0001.0050 in welcher X einen reaktionsfähigen, während der Reaktion sieh abspaltenden Rest bedeutet, mit Diäthylamin umsetzt. Das auf diese -Iffeise erhaltene Diäthylaminoessigsäure-N-(3-o-chlor- , EMI0002.0001 plxeno-xy-propyl-2)-metlxylamid <SEP> bildet <SEP> ein <SEP> farb loses, <SEP> unter <SEP> 0,08 <SEP> mm <SEP> bei <SEP> 160-l62 <SEP> sieden des <SEP> Öl. <tb> Das <SEP> neue <SEP> Axnicl <SEP> soll <SEP> als <SEP> Lokalanästlxetikum <tb> und <SEP> als <SEP> Zwischenprodukt <SEP> Verwendung <SEP> fin den. PATENT CLAIM: Process for the preparation of a new basic substituted fatty acid amide, characterized in that one is a compound of the formula EMI0001.0050 in which X denotes a reactive radical which is split off during the reaction, with diethylamine. The diethylaminoacetic acid-N- (3-o-chloro-, EMI0002.0001 plxeno-xy-propyl-2) -metlxylamid <SEP> forms <SEP> a <SEP> colorless, <SEP> under <SEP> 0.08 <SEP> mm <SEP> at <SEP> 160-l62 <SEP > simmer the <SEP> oil. <tb> The <SEP> new <SEP> Axnicl <SEP> should <SEP> as a <SEP> local anesthetic <tb> and <SEP> as <SEP> intermediate product <SEP> use <SEP>. EMI0002.0002 UNTDRAN <SEP> SPRL <SEP> CII <tb> Verfahren <SEP> nach <SEP> Patentansprueli, <SEP> cladureh <tb> < -ekennzeielmet, <SEP> dass <SEP> nxan <SEP> ein <SEP> @a@ogenessi; säure-V <SEP> - <SEP> ( <SEP> 3-o-c <SEP> hlor-phenosy- <SEP> propyl- <SEP> 2 <SEP> @ <SEP> -met <SEP> h@-1 amid <SEP> und <SEP> Diäthylamin <SEP> reagieren <SEP> lässt. EMI0002.0002 UNTDRAN <SEP> SPRL <SEP> CII <tb> Procedure <SEP> according to <SEP> patent claims, <SEP> cladureh <tb> <-ekennzeielmet, <SEP> that <SEP> nxan <SEP> a <SEP> @ a @ ogenessi; acid-V <SEP> - <SEP> (<SEP> 3-oc <SEP> hlor-phenosy- <SEP> propyl- <SEP> 2 <SEP> @ <SEP> -met <SEP> h @ -1 amide <SEP> and <SEP> diethylamine <SEP> reacts <SEP> causes.
CH311665D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311665A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311665T 1952-06-08
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311665A true CH311665A (en) 1955-11-30

Family

ID=25735398

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311665D CH311665A (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) CH311665A (en)

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