CH311617A - Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). - Google Patents

Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).

Info

Publication number
CH311617A
CH311617A CH311617DA CH311617A CH 311617 A CH311617 A CH 311617A CH 311617D A CH311617D A CH 311617DA CH 311617 A CH311617 A CH 311617A
Authority
CH
Switzerland
Prior art keywords
methyl
anilide
halogen
fatty acid
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 CH311617A publication Critical patent/CH311617A/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

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

Description

  

  Verfahren zur Herstellung eines neuen basisch     substituierten        Fettsäure-          (2-halogen-6-methyl-anilids).            Gegenstand    des vorliegenden Patentes bil  det ein Verfahren zur Herstellung eines neuen       basisch        substituierten        Fettsälure-(2-hal.ogen-6-          methyl-a.nilids),    welches dadurch gekennzeich  net ist, dass man eine Verbindung der Formel  
EMI0001.0009     
    in     welcher    X einen reaktionsfähigen, während  der Reaktion sich 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  ren     Substituenten,    wie z. B. einer     Alky1sul-          fonyloxy-    oder     Arylsulfonyloxygruppe,    beste  hen.

   Der Austausch der Gruppe X gegen den       2-Methyl-piperidinrest    erfolgt.     z."B.    durch ein  faches Erwärmen mit     2-Methyl-piperidin    ge  gebenenfalls in Gegenwart eines basisch re  agierenden Kondensationsmittels oder von     2-          Methyl-piperidin    im     -Überschuss.    Das     N-2-Me-          thy        1-piperidino-a.cet-(2'-ehlor-6'-methyl-anilid)     ist ein Öl, das nach einiger Zeit zu farblosen,  bei 97-98  schmelzenden Kristallen erstarrt.  Das Hydrochlorid der Base schmilzt bei<B>177</B>  bis l80 .  



  Das neue     Anilid    soll als Lokalanästhetikum  und als Zwischenprodukt zur     Herstellung    wei  terer Derivate Verwendung finden.    <I>Beispiel:</I>  36 Gewichtsteile     Chloracet-(2-chlor-6-me-          thyl-anilid)    (gewonnen durch Umsetzen von     2-          Chlor-6-methyl-anilin    mit     Chloracetylchlorid     in Gegenwart von     Natriumaeetat,        Schmp.    140  bis 141 ) werden in 7 0 Gewichtsteilen Äthanol  suspendiert und mit 42     Gewichtsteilen        2-Me-          thyl-piperidin    versetzt.

   Die Temperatur     steigt     dabei leicht an und ein grosser Teil     des    Reak  tionsgemisches geht in Lösung. Nun wird wäh  rend 4 Stunden bei Zimmertemperatur ge  rührt und dann einige Stunden bei 65-75 .  Eine Probe mit Wasser und nachfolgend mit  verdünnter Salzsäure     versetzt    ergibt wieder  Lösung des ausgefallenen Niederschlages. Mit  Wasserdampf wird hierauf der Alkohol und  das überschüssige     2-1Vlethyl-piperidin    abgebla  sen und nach dem Erkalten das zurückblei  bende Öl in Äther aufgenommen. Nach dem  Trocknen der ätherischen Lösung und Ver  jagen des Lösungsmittels verbleibt ein Öl, das  durch Vakuumdestillation gereinigt wird.

   Man  erhält 40     Gewichtsteile    reines     N-2-Methyl-          piperidino-acet-(2'-chlor-6'-methyl-anilid),    was       einer        Ausbeute        von        87        %        entspricht.        Die        Um-          setzung    mit     2-Methyl-piperidin    kann auch in  Benzol     stattfinden.  



  Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). The subject of the present patent bil det a process for the preparation of a new basic substituted fatty acid (2-halo-6-methyl-a.nilids), which is characterized in that a compound of the formula
EMI0001.0009
    in which X is a reactive radical which is split off during the reaction, is reacted with 2-methylpiperidine.



  The radical X can be in a halogen atom or other suitable reactive substituents for replacement with the basic radical, such as. B. an alky1sulfonyloxy or arylsulfonyloxy group, best hen.

   The group X is exchanged for the 2-methylpiperidine residue. z. "E.g. by single heating with 2-methyl-piperidine, optionally in the presence of a basic-reacting condensing agent or of 2-methyl-piperidine in excess. The N-2-methy 1-piperidino-a.cet - (2'-chloro-6'-methyl-anilide) is an oil that solidifies after some time to colorless crystals that melt at 97-98. The hydrochloride of the base melts at <B> 177 </B> to 180.



  The new anilide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. <I> Example: </I> 36 parts by weight of chloroacet- (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with chloroacetyl chloride in the presence of sodium acetate, melting point 140 to 141) are suspended in 70 parts by weight of ethanol and mixed with 42 parts by weight of 2-methylpiperidine.

   The temperature rises slightly and a large part of the reaction mixture goes into solution. The mixture is then stirred for 4 hours at room temperature and then for a few hours at 65-75. A sample with water and then mixed with dilute hydrochloric acid results in a solution of the precipitate. The alcohol and the excess 2-1Vlethyl-piperidine are then blown off with steam and, after cooling, the remaining oil is taken up in ether. After the essential solution has dried and the solvent has been chased away, an oil remains which is purified by vacuum distillation.

   40 parts by weight of pure N-2-methylpiperidino-acet- (2'-chloro-6'-methyl-anilide) are obtained, which corresponds to a yield of 87%. The reaction with 2-methylpiperidine can also take place in benzene.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6- methyl-anilids), dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0002.0001 in welcher X einen reaktionsfähigen, während der Reaktion sieh abspaltenden Rest bedeutet, mit 2-Methyl=piperidin umsetzt. Das auf diese Weise erhaltene N-2-Methyl-piperidino-acet- (2'-chlor-6'-methyl-anilid) bildet ein Öl, das nach einiger Zeit. zu farblosen, bei 97-98 schmelzenden Kristallen erstarrt.. PATENT CLAIM: Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-anilide), characterized in that a compound of formula EMI0002.0001 in which X denotes a reactive radical which is split off during the reaction, with 2-methyl = piperidine. The N-2-methyl-piperidino-acet- (2'-chloro-6'-methyl-anilide) obtained in this way forms an oil that after some time. solidified to colorless crystals melting at 97-98. Das Hydro chlorid der Base schmilzt bei l_77-180 . Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein Halogenacet-(2- chlor-6-methyl-anilid) mit 2-llethyl-piperidirl reagieren lässt. The hydrochloride of the base melts at l_77-180. The new anilide will be used as a local anesthetic and as an intermediate product. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that a halogen acetone (2-chloro-6-methyl-anilide) is allowed to react with 2-llethyl-piperidirl.
CH311617D 1952-02-25 1952-02-25 Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). CH311617A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311617T 1952-02-25
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311617A true CH311617A (en) 1955-11-30

Family

ID=25735350

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311617D CH311617A (en) 1952-02-25 1952-02-25 Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).

Country Status (1)

Country Link
CH (1) CH311617A (en)

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