CH311623A - 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
CH311623A
CH311623A CH311623DA CH311623A CH 311623 A CH311623 A CH 311623A CH 311623D A CH311623D A CH 311623DA CH 311623 A CH311623 A CH 311623A
Authority
CH
Switzerland
Prior art keywords
anilide
methyl
production
fatty acid
halogen
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 CH311623A publication Critical patent/CH311623A/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     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-anilids),    welches dadurch gekennzeich  net ist, dass     mann    eine Verbindung der Formel  
EMI0001.0009     
    in welcher X einen     reaktionsfähigen,    während  der Reaktion sich abspaltenden Rest     bedeutet,     mit.

       Dimethylamin        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     Grippe    X gegen den       Dimethylaminrest    erfolgt z.

   B. durch einfaches       Erwärmen    mit     Dimethylamin    gegebenenfalls  in Gegenwart     eines    basisch reagierenden Kon  densationsmittels oder von     Dimethylamin    im       L'berschuss.    Das     ss    -     Dimethylamino    -     propion-          säure-(2-chlor-6-methyl-anilid)    ist ein farbloses,  auch im Hochvakuum nicht     unzerset.zt    sieden  des Öl. Das Hydrochlorid der Base schmilzt  bei 77,5-79,5 .  



  Das neue     Anilid    soll als Lokalanästhetikum  und als     Zwischenprodukt        zur    Herstellung wei  terer Derivate Verwendung finden.    <I>Beispiel:</I>  30     Gewichtsteile        ss-Chlorpropionsäure-(2-          chlor-6-methyl-anilid)    (gewonnen durch Um  setzen von     2-Chlor-6-methyl-anilin    mit     ss-Chlor-          propionylchlorid    in Gegenwart von     Natrüun-          acetat,        Schmp.    l09-112 )

   werden in 180 Ge  wichtsteilen Methanol suspendiert und mit<B>135</B>  Gewichtsteilen wässriger     33o/oiger        Dimethyl-          aminlösung        versetzt.    Die Temperatur steigt  dabei leicht an und ein grosser Teil des Re  aktionsgemisches geht in Lösung. Nun wird  während 1 Stunden bei Zimmertemperatur  gerührt und dann     einige    Stunden bei 60-70 .

    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     Dimethylamin    abgeblasen  und nach dem Erkalten und Sättigen der       wässrigen    Lösung mit     Natriumchlorid    das zu  rückbleibende Öl in Äther aufgenommen. Nach  dem Trocknen der ätherischen Lösung und  Verjagen des     Lösungsmittels    verbleibt ein Öl,  das     durch    Überführen in das Hydrochlorid  gereinigt wird.

   Man erhält 65 Gewichtsteile  reines     ss-Dimethylamino-propionsäure-(2-chlor-          6-methyl-anilid).    Die Umsetzung mit     Dime-          thylamin    kann auch in Benzol stattfinden.



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

       Dimethylamine converts.



  The radical X can be in a halogen atom or another for the exchange against the basic radical. Suitable reactive substituents such. B. an alkylsulfonyloxy or arylsulfonyloxy group, best hen. The exchange of flu X against the dimethylamine residue takes place z.

   B. by simply heating with dimethylamine, optionally in the presence of a basic reacting Kon densantsmittel or of dimethylamine in excess. The ss - dimethylamino - propionic acid (2-chloro-6-methyl-anilide) is a colorless oil that does not boil undecomposed even in a high vacuum. The base hydrochloride melts at 77.5-79.5.



  The new anilide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. <I> Example: </I> 30 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, m.p. 109-112)

   are suspended in 180 parts by weight of methanol and <B> 135 </B> parts by weight of aqueous 33% dimethylamine solution are added. The temperature rises slightly and a large part of the reaction mixture goes into solution. The mixture is then stirred for 1 hour at room temperature and then for a few hours at 60-70.

    A sample with water and then mixed with dilute hydrochloric acid results. again dissolution of the precipitate. The alcohol and the excess dimethylamine are then blown off with steam and, after the aqueous solution has cooled and saturated with sodium chloride, the remaining oil is taken up in ether. After drying the essential solution and driving off the solvent, an oil remains which is purified by converting it into the hydrochloride.

   65 parts by weight of pure β-dimethylamino-propionic acid (2-chloro-6-methyl-anilide) are obtained. The reaction with dimethylamine can also take place in benzene.

Claims (1)

PATENTANTSPRUCH Verfahren zur Herstellung eines neuen basisch substituierten Fett8äure-(2-halogen-6- methyl anilids), dadurch gekennzeichnet., dass man eine Verbindune der Formel EMI0002.0004 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest. bedeutet, mit. Dimethylamin umsetzt. PATENT CLAIM Process for the production of a new basic substituted fatty acid (2-halo-6-methyl anilide), characterized in that one is a compound of the formula EMI0002.0004 in which X is a reactive radical which is split off during the reaction., with. Dimethylamine converts. Das auf diese Weise erhaltene ,8 - Dimethylamino - propion- säure-(2-ehlor-6-methyl-anilid) bildet ein farb- loses, aüeh iin HOelivakunni nicht unzersetzt siedendes Öl. Das Hydroelilorid der Base schmilzt bei 77,5-79,5 . Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt. Verwendung finden. The 8-dimethylamino-propionic acid (2-chloro-6-methyl-anilide) obtained in this way forms a colorless oil that does not boil undecomposed even in HOelivakunni. The hydroeliloride of the base melts at 77.5-79.5. The new anilide is said to be used as a local anesthetic and as an intermediate. Find use. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein /3-Halogen-pro- pionsäure-(2-ehlor-6-nietlicl-aniiid) mit. Dinie- thylamin reagieren lässt. SUBCLAIM: Process according to claim, characterized in that a / 3-halo-propionic acid (2-chloro-6-nietlicl-aniiide) is used with. Lets diethylamine react.
CH311623D 1952-02-25 1952-02-25 Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). CH311623A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311623T 1952-02-25
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311623A true CH311623A (en) 1955-11-30

Family

ID=25735356

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311623D CH311623A (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) CH311623A (en)

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