CH328669A - 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
CH328669A
CH328669A CH328669DA CH328669A CH 328669 A CH328669 A CH 328669A CH 328669D A CH328669D A CH 328669DA CH 328669 A CH328669 A CH 328669A
Authority
CH
Switzerland
Prior art keywords
sep
fatty acid
acid amide
production
substituted fatty
Prior art date
Application number
Other languages
German (de)
Inventor
Hans Dr Suter
Hans Dipl Chem Zutter
Widler Hans
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 CH328669A publication Critical patent/CH328669A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)

Description

  

      Verfahren        zur    Herstellung eines neuen basisch     substituierten        Fettsäureamides            Gegenstand    des vorliegenden Patentes bil  det ein Verfahren zur     Herstellung    eines neuen  basisch substituierten     Fettsäureamvdes,    wel-         ches    dadurch gekennzeichnet ist, dass man  eine     Verbindung    der Formel  
EMI0001.0010     
    in welcher X einen     reaktionsfähigen,    wäh  rend der Reaktion sich abspaltenden Rest be  deutet, mit     Pyrrolidin        umsetzt.     



  Der Rest X kann in     einem    Halogenatom  oder einem sonstigen für den Austausch ge  gen den basischen Rest geeigneten reaktions  fähigen     Substituenten,    wie z. B. einer     A'lkyl-          sulfonyloxy-    oder     Arylsidfonyloxygruppe    be  stehen. Der Austausch der Gruppe X gegen  den     Pyrrolidinrest    erfolgt z.

   B. durch ein-    Faches     Erwärmen    mit     Pyrrolidin,        gegebenen-          fa@lis    in Gegenwart     eines        basisch        reagierenden          Kondensationsmittels    oder von     Pyrrolidin    im  Überschuss. Das     N-[1-(4'-#Butoxy-phenoxy)-          äthyl-2]-N-methylpyrrolidinoacetamid    ist ein  farbloses, unter 0,04 mm bei 181 bis     182     sie  dendes Öl.  



  Das neue     Amid    soll als Lokalanästhetikum       und        als        Zwisehenprodukt    zur     HerstelUmg    wei  terer     Derivate    Verwendung finden.    <I>Beispiel</I>    30g     N-[1-(4'-Butoxy-phenoxy)-äthyl-2]-          .\T-methyl-chloracetamid    und 11g     Pyrrolidin     werden zusammen in 50     cm3        abs.    Benzol  6 Stunden auf dem Wasserbad erhitzt.

   Das     Re-          aktionsgemisch    wird mit     Wasser    ausgeschüttelt  und     dann.    mit 2n     Salzsäure    ausgezogen. Dar  auf wird der salzsaure Auszug mit Äther ex  trahiert, unter Eiskühlung mit     konzentrierter     Natronlauge versetzt und das     ausgeschiedene            Ö!1    in Äther aufgenommen. Nach dem Trock  nen der Ätherauszüge über     Pottasche        wird    der  Äther verdampft     und    der Rückstand im Hoch  vakuum destilliert.  



  Dabei     gewinnt    man das unter 0,04 mm bei       181-1829    siedende     N-[1-(4'-Butoxy-phenoxy)-          äthyl-2]    N -     methyl    -     pyrrolidino    -     aeetamid    als  farbloses, säurelösliches Öl.



      Process for the Production of a New Basically Substituted Fatty Acid Amide The subject of the present patent is a process for the production of a new base substituted fatty acid amide, which is characterized in that a compound of the formula
EMI0001.0010
    in which X is a reactive radical which is split off during the reaction, reacts with pyrrolidine.



  The radical X can be in a halogen atom or other suitable reactive substituents for the exchange against the basic radical, such as. B. an A'lkyl- sulfonyloxy or Arylsidfonyloxygruppe be available. The exchange of the group X against the pyrrolidine radical takes place, for.

   B. by one-fold heating with pyrrolidine, given fa @ lis in the presence of a basic condensing agent or pyrrolidine in excess. The N- [1- (4 '- # Butoxyphenoxy) - ethyl-2] -N-methylpyrrolidinoacetamide is a colorless, below 0.04 mm at 181 to 182 sie Dendes oil.



  The new amide is to be used as a local anesthetic and as an intermediate product for the manufacture of further derivatives. <I> Example </I> 30 g of N- [1- (4'-butoxy-phenoxy) -ethyl-2] -. \ T-methyl-chloroacetamide and 11 g of pyrrolidine are combined in 50 cm3 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, concentrated sodium hydroxide solution is added while cooling with ice, and the oil 1 that has separated out is 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- [1- (4'-butoxyphenoxy) -ethyl-2] N-methyl-pyrrolidino-aetamide boiling below 0.04 mm at 181-1829 is obtained as a colorless, acid-soluble oil.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines neuen ba- sisch substituierten Fettsäureamides, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0002.0001 EMI0002.0002 in <SEP> welcher <SEP> X <SEP> einen <SEP> reaktionsfähigen, <SEP> während <tb> der <SEP> Reaktion <SEP> sich <SEP> abspaltenden <SEP> Rest <SEP> bedeutet, <tb> mit <SEP> Pyrrolidin <SEP> umsetzt. <SEP> Das <SEP> so <SEP> erhaltene <SEP> N-[1 (4'-Butoxy <SEP> - <SEP> phenoxy) <SEP> -äthyl-'2]-N-methyl-pyr rolidino-acetamid <SEP> bildet <SEP> ein <SEP> farbloses, <SEP> unter <tb> 0,04 <SEP> mm <SEP> bei <SEP> 181-1892 <SEP> siedendes <SEP> Öl. PATENT CLAIM Process for the preparation of a new basic substituted fatty acid amide, characterized in that a compound of the formula EMI0002.0001 EMI0002.0002 in <SEP> which <SEP> X <SEP> a <SEP> reactive, <SEP> during <tb> of the <SEP> reaction <SEP> <SEP> separating <SEP> rest <SEP> means <tb> with <SEP> reacts pyrrolidine <SEP>. <SEP> The <SEP> so <SEP> obtained <SEP> N- [1 (4'-butoxy <SEP> - <SEP> phenoxy) <SEP> -äthyl-'2] -N-methyl-pyr rolidino- acetamid <SEP> forms <SEP> a <SEP> colorless, <SEP> under <tb> 0.04 <SEP> mm <SEP> with <SEP> 181-1892 <SEP> boiling <SEP> oil. EMI0002.0003 UNTERA'NSPRUCI4 <tb> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> dadurch <tb> gekennzeichnet, <SEP> dass <SEP> man <SEP> ein <SEP> N <SEP> [1-(4'-Butoxy phenoxy)-äthyl-2<B>]</B> <SEP> -N-methyl <SEP> - <SEP> halogenacetamid <tb> mit <SEP> Pvrrolidin <SEP> reagieren <SEP> 'lässt. EMI0002.0003 UNDERA'NSPRUCI4 <tb> Method <SEP> according to <SEP> patent claim, <SEP> thereby <tb> marked, <SEP> that <SEP> one <SEP> a <SEP> N <SEP> [1- (4'-butoxy phenoxy) -äthyl-2 <B>] </B> <SEP> - N-methyl <SEP> - <SEP> haloacetamide <tb> reacts with <SEP> pvrrolidin <SEP> <SEP> '.
CH328669D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide CH328669A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH328669T 1952-06-08
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH328669A true CH328669A (en) 1958-03-15

Family

ID=25735445

Family Applications (1)

Application Number Title Priority Date Filing Date
CH328669D CH328669A (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) CH328669A (en)

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