CH311618A - 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).

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Publication number
CH311618A
CH311618A CH311618DA CH311618A CH 311618 A CH311618 A CH 311618A CH 311618D A CH311618D A CH 311618DA CH 311618 A CH311618 A CH 311618A
Authority
CH
Switzerland
Prior art keywords
anilide
methyl
halogen
production
new basic
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 CH311618A publication Critical patent/CH311618A/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     Pettsä-Lire-(2-halogen-6-          niet.liyl-anilids),        welches    dadurch gekennzeich  net ist, dass man eine Verbindung der     Formel     
EMI0001.0012     
         iii        welcher    N einen reaktionsfähigen,

   während  der Reaktion sieh abspaltenden Rest bedeutet,       reit.        2,6-Dimetliyl-piperidin    umsetzt.  



       Der    Rest. N kann in einem Halogenatom  oder einem sonstigen für den Austausch gegen  den basischen Rest geeigneten reaktionsfälli  gen     Substituenten,    wie z. B.     einer        AlkvIsul-          fotivio.xv-        oder        lirylsulfonvloxygriippe,    beste  lien. Der Austausch der Gruppe N gegen den       2,6-Dimetliyl-piperidinrest    erfolgt z.

   B. durch       einfaches    Erwärmen mit     2,6-Dimethyl-piperi-          din    gegebenenfalls in Gegenwart eines basisch  reagierenden Kondensationsmittels oder von       2,6-Diniethv        1-piper        idin    im     L        bersehuss.    Das     N-          2,6-Dimetliyl.-piperidino    -     aeet        -(2'-    chlor- 6'-     me-          thvl-anilid)        ist    ein Öl, das nach einiger Zeit       zii    farblosen,

   bei 130  schmelzenden Kristallen  erstarrt. Das Hydrochlorid der Base schmilzt  bei 240 .  



  Das neue     Anilid    soll als Lokalanästhetikum       und    als Zwischenprodukt     zur        Herstellung    wei  terer Derivate Verwendung finden.         Beispiel:

       36     Gewichtsteile        Chloracet-(2-chlor-6-me-          thyl-anilid)    (gewonnen durch Umsetzen von       2-Chlor-6-methyl-anilin    mit     Chloracetylchlorid     in Gegenwart von     Natriumaeet.at,        Schmp.    140  bis     141 )    werden in 70 Gewichtsteilen     Äthanol     suspendiert und mit 57     Gewiehtsteilen        2,6-          Dimethyl-piperidin    versetzt. Die Temperatur  steigt dabei leicht an, und ein grosser Teil des  Reaktionsgemisches geht. in Lösung.

   Nun wird  während 4 Stunden bei Zimmertemperatur  gerührt 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     2,6-Dimethyl-piperidin    ab  geblasen und nach dem Erkalten das zurück  bleibende Öl. in Äther aufgenommen. Nach  dem Trocknen der ätherischen Lösung und  Verjagen des     Lösungsmittels    verbleibt ein Öl,  das durch     Vakuumdestillation    gereinigt wird.

    Man erhält 32     Gewichtsteile        reines        N-2,6-Di-          methyl-piperidino-acet    -     (2'-chlor-6'-        methyl-ani-          lid),        was        einer        Ausbeute        von        65%        entspricht.     Die     Umsetzung    mit     2,6-Dimethyl-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 Pettsä-Lire- (2-halogen-6- niet.liyl-anilids), which is characterized in that a compound of the formula
EMI0001.0012
         iii which N is a reactive,

   during the reaction see separating residue means riding. 2,6-Dimetliyl-piperidine converts.



       The radical. N can be in a halogen atom or any other suitable reactive substituents for replacement with the basic radical, such as. B. an AlkvIsul- fotivio.xv- or lirylsulfonvloxyfluippe, best lien. The exchange of the group N against the 2,6-Dimetliyl-piperidinrest takes place z.

   B. by simply heating with 2,6-dimethyl-piperidine, optionally in the presence of a basic condensing agent or of 2,6-diniethv 1-piperidine in excess. The N-2,6-Dimetliyl.-piperidino-aeet- (2'-chloro-6'-methvl-anilide) is an oil that after some time becomes colorless,

   solidified at 130 melting crystals. The base hydrochloride melts at 240.



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

       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 Natriumaeet.at, melting point 140 to 141) are 70 parts by weight Suspended ethanol and treated with 57 parts by weight of 2,6-dimethylpiperidine. The temperature rises slightly and a large part of the reaction mixture leaves. in 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 2,6-dimethylpiperidine are then blown off with steam and the oil that remains after cooling. absorbed into ether. After the essential solution has dried and the solvent has been driven off, an oil remains which is purified by vacuum distillation.

    32 parts by weight of pure N-2,6-dimethyl-piperidino-acet - (2'-chloro-6'-methyl-anilide) are obtained, which corresponds to a yield of 65%. The reaction with 2,6-dimethylpiperidine can also take place in benzene.

Claims (1)

PATEN TANSPR.UCH Verfahren zur Herstellung eines neuen basisch substituierten Pettsä-Lire-(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 2,6-Dimethyl-piperidin umsetzt. PATEN TANSPR.UCH Process for the preparation of a new basic substituted Pettsä-Lire- (2-halogen-6-methyl-anilide), characterized in that a compound of the formula EMI0002.0001 in which X denotes a reactive radical which is split off during the reaction, with 2,6-dimethylpiperidine. Das auf diese Weise erhaltene N-2,6-Dimethyl-piperi- dino-acet-(2'-chlor-6'-methyl-anilid) bildet ein Öl, das nach einiger Zeit zu farblosen, bei 130 schmelzenden Kristallen erstarrt. Das Hydrochlorid der Base sehmilzt bei 240 . Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. The N-2,6-dimethyl-piperidino-acet- (2'-chloro-6'-methyl-anilide) obtained in this way forms an oil which solidifies after a while to form colorless crystals which melt at 130. The base hydrochloride melts at 240. The new anilide will be used as a local anesthetic and as an intermediate product. U NT1:RAN SPRI; CIl Verfahren nach Patentanspruch, dadurrli gekennzeiehnet, dass man ein Halogenaeet-(2- chlor-6-methyl-anilid) mit 2,6-Dimethyl-pipe- ridin reagieren lässt. U NT1: RAN SPRI; CIl method according to patent claim, dadurrli gekennzeiehnet that a Halogenaeet- (2-chloro-6-methyl-anilide) is allowed to react with 2,6-dimethyl-piperidine.
CH311618D 1952-02-25 1952-02-25 Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). CH311618A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311618T 1952-02-25
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311618A true CH311618A (en) 1955-11-30

Family

ID=25735351

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311618D CH311618A (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) CH311618A (en)

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