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CH311628A - 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
CH311628A
CH311628A CH311628DA CH311628A CH 311628 A CH311628 A CH 311628A CH 311628D A CH311628D A CH 311628DA CH 311628 A CH311628 A CH 311628A
Authority
CH
Switzerland
Prior art keywords
anilide
methyl
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 CH311628A publication Critical patent/CH311628A/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     Fettsäure-(2-halogen-6-          methyl-a,nilids),        welches    dadurch gekennzeich  net     isst,    dass man eine Verbindung der Formel  
EMI0001.0011     
    in welcher X einen     reaktionsfähigen,    während  der Reaktion sich abspaltenden Rest bedeutet,  mit     2,

  6-Dimethyl-piperidin    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     Alkylsul-          fonyloxy-    oder     Arylsulfonyloxygruppe,    beste  hen. Der Austausch der Gruppe X gegen den       2,6-Dimethyl-piperidinrest    erfolgt z.

   B. durch  einfaches Erwärmen mit     2,6-Dimethyl-piperi-          din    gegebenenfalls in Gegenwart eines basisch  reagierenden Kondensationsmittels oder von       2,6-Dimethyl-piperidin    im     L'berschuss.    Das ss  (2,6-Dimethyl-piperidino)     -propionsäure-        (2'-          chlor-6'-methyl-anilid)    ist ein farbloses Kri  stallpulver. Das Hydrochlorid der Base  schmilzt, bei 237,5-239,5 .  



  Das neue     Anilid    soll als Lokalanästhetikum  und als     Zwisehenprodukt    zur Herstellung wei  terer Derivate Verwendung finden.  



       Beispiel:     29 Gewichtsteile     ss-Chlor-propionsäiire-(2-          chlor-6-methyl-anilid)    (gewonnen durch Um-    setzen von     2-Chlor-6-methyl-anilin    mit     ,ss-Chlor-          propionyl-chlorid    in Gegenwart von Natrium  acetat,     Schmp.    109-112 ) werden in 80 Ge  wichtsteilen Äthanol     suspendiert    und mit 42,5  Gewichtsteilen     2,6-Dimethylpiperidin    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 .

   Mit Wasserdampf wird  hierauf der Alkohol und das     überschüssige          2,6-Dimethyl-piperidin    abgeblasen und nach  dem Erkalten das zurückbleibende Öl in Äther  aufgenommen. Nach dem Trocknen der ätheri  schen Lösung und Verjagen des Lösungs  mittels verbleibt. ein farbloses Kristallpulver.

    Man erhält 35 Gewichtsteile     reines        ss-(2,6-Di-          methyl-        pip        eridino)    -     propionsäure    - (2'-     chlor-6'-          methyl-anilid).    Die Umsetzung mit     2,6-Di-          methyl-piperidin    kann auch in Benzol statt  finden.



  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-halogen-6-methyl-a, nilids), which is characterized by eating a compound of the formula
EMI0001.0011
    in which X is a reactive radical which is split off during the reaction, with 2,

  6-dimethylpiperidine converts.



  The radical X can be in a halogen atom or other suitable reactive substituents for replacement with the basic radical, such as. B. an alkylsulfonyloxy or arylsulfonyloxy group, best hen. The exchange of group X against the 2,6-dimethyl-piperidine radical takes place, for.

   B. by simply heating with 2,6-dimethyl-piperidine optionally in the presence of a basic condensing agent or 2,6-dimethyl-piperidine in excess. The ss (2,6-dimethyl-piperidino) -propionic acid- (2'-chloro-6'-methyl-anilide) is a colorless crystal powder. The base hydrochloride melts, at 237.5-239.5.



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



       Example: 29 parts by weight of ß-chloropropionic acid (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with ß-chloropropionyl chloride in the presence of sodium acetate, melting point 109-112) are suspended in 80 parts by weight of ethanol, and 42.5 parts by weight of 2,6-dimethylpiperidine are added. 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.

   The alcohol and the excess 2,6-dimethylpiperidine are then blown off with steam and, after cooling, the oil that remains is taken up in ether. After the ethereal solution has dried and the solvent has been driven off, it remains. a colorless crystal powder.

    35 parts by weight of pure ss- (2,6-dimethylpiperidino) propionic acid (2'-chloro-6'-methyl-anilide) are obtained. The reaction with 2,6-dimethylpiperidine can also take place in benzene.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6- methyP@anilids), dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0001.0053 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit 2,6-Dimethyl-piperidin umsetzt. PATENT CLAIM: Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyP @ anilids), characterized in that a compound of the formula EMI0001.0053 in which X is a reactive radical which is split off during the reaction, is reacted with 2,6-dimethylpiperidine. Das auf diese Weise erhaltene ss-(2,6-Dimethyl-piperi- dino) - propionsäure- (2'-ehlor-6'-methy 1-anilid ) bildet ein farbloses Kristallpulver. Das Hydro- chlorid der Base schmilzt bei '237,5-239,50. Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden- UNTERANSPRUCH: The ss- (2,6-dimethyl-piperidino) propionic acid (2'-chloro-6'-methy 1-anilide) obtained in this way forms a colorless crystal powder. The hydrochloride of the base melts at 237.5-239.50. The new anilide is to be used as a local anesthetic and as an intermediate product. Verfahren naeh Patentanspruch, dadureh gekennzeichnet, dass man ein ss-Halogen-pro- pionsäure-(2-ehlor-6-met.hvl-anilid) mit 2,6 Dimethvl.-piperidin rea'pieren lässt. Process according to patent claim, characterized in that an β-halo-propionic acid (2-chloro-6-met.hvl-anilide) is allowed to react with 2,6 dimethyl piperidine.
CH311628D 1952-02-25 1952-02-25 Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). CH311628A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311628T 1952-02-25
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311628A true CH311628A (en) 1955-11-30

Family

ID=25735361

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311628D CH311628A (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) CH311628A (en)

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