CH311639A

CH311639A - Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).

Info

Publication number: CH311639A
Authority: CH
Inventors: Aktiengesellschaft Cilag
Original assignee: Cilag Ag
Priority date: 1952-02-25
Filing date: 1952-02-25
Publication date: 1955-11-30

Description

  

  



     Verfabren    zur Herstellung eines neuen basisch substituierten   Fettsäure-       (2-halogen-6-methyl-anilids).   



   Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten FettsÏure- (2-halogen-6   methyl-anilids), welches dadurch gekennzeich-    net ist dass man eine Verbindung der Formel
EMI1.1     
 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit ¯thylamin umsetzt.



   Der Rest X kann in einem Halogenatom oder einem sonstigen f r den Austausch gegen den basischen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer   Alkylsulfonyl-    oxy-oder Arylsulfonyloxygruppe, bestehen.



  Der   Austauseh    der Gruppe X gegen den   Äthyl aminrest    erfolgt z. B. durch einfaches   Erwärmen mit Äthylamin gegebenenfalls    in Gegenwart eines basisch reagierenden   Konden-    sationsmittels oder   vonÄthylaminimÜber-    schuss. Das   a-N-ät. hylamino-capronsäure-    (2  ehlor-6-methyl-anilid)    ist ein farbloses, sÏure  losliehes öl.    Das   Hydroehlorid    der Base schmilzt bei   151-153 .   



   Das neue Anilid soll als   Lokalanästhetikum    und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden.



   Beispiel :
33 Gewichtsteile   a-Brom-capronsäure-    (2  ehlor-6-methyl-anilid)    (gewonnen durch Umsetzen von 2-Chlor-6-methyl-anilin mit a-Bromeapronsäurebromid in Gegenwart von Na  triumacetat,Sehmp.132")    werden in 150 Ge  wichtsteilen Äthanol    suspendiert und mit 100    Gewichtsteilen wässriger 70% iger Athylamin-    lösung versetzt. Die Temperatur steigt dabei leicht an, und ein grosser Teil des Reaktionsgemisches geht in L¯sung Nun wird während 4 Stunden bei Zimmertemperatur gerührt und dann einige Stunden bei   65-75 .    Das Ganze wird auf Wasser gegossen, die wässrige Lösung mit Koehsalz gesÏttigt, das sich   abscheidende    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 29 Gewichtsteile reines a   N-Athylamino-capronsäure- (2-chlor-6-methyl-    anilid). Die Umsetzung mit   Äthylamin    kann auch in Benzol stattfinden.  



   PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten   Fettsäure- (2-halogen-6-    methyl-anilids), dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.2     
 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.





  



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



   The subject of the present patent forms a process for the preparation of a new basic substituted FettsÏure- (2-halogen-6-methyl-anilids), which is characterized by the fact that a compound of the formula
EMI1.1
 in which X is a reactive radical which is split off during the reaction, reacts with ¯thylamine.



   The radical X can be in a halogen atom or another reactive substituent suitable for replacement with the basic radical, such as e.g. B. an alkylsulfonyl oxy or arylsulfonyloxy group exist.



  The exchange of group X against the ethyl amine residue z. B. by simply heating with ethylamine, if necessary in the presence of a basic condensing agent or of excess ethylamine. The a-N-ät. Hylamino-caproic acid (2-chloro-6-methyl-anilide) is a colorless, acid-free oil. The hydrochloride of the base melts at 151-153.



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



   Example:
33 parts by weight of a-bromo-caproic acid (2 ehlor-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with a-bromoeapronic acid bromide in the presence of sodium acetate, Sehmp.132 ") are in 150 Parts by weight of ethanol are suspended and 100 parts by weight of 70% aqueous ethylamine solution are added. The temperature rises slightly and a large part of the reaction mixture is dissolved. The mixture is then stirred for 4 hours at room temperature and then for a few hours at 65- 75. The whole thing is poured onto water, the aqueous solution is saturated with salt, and the oil which separates out 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. 29 parts by weight of pure α-N-ethylamino-caproic acid (2-chloro-6-methyl anilide) are obtained. The reaction with ethylamine can also take place in benzene.



   PATENT CLAIM:
Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-anilide), characterized in that a compound of the formula
EMI1.2
 

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims

** WARNING ** Beginning of CLMS field could overlap end of DESC **.

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

The subject of the present patent forms a process for the preparation of a new basic substituted FettsÏure- (2-halogen-6-methyl-anilids), which is characterized by the fact that a compound of the formula EMI1.1 in which X is a reactive radical which is split off during the reaction, reacts with ¯thylamine.

The radical X can be in a halogen atom or another reactive substituent suitable for replacement with the basic radical, such as e.g. B. an alkylsulfonyl oxy or arylsulfonyloxy group exist.

The exchange of group X against the ethyl amine residue z. B. by simply heating with ethylamine, if necessary in the presence of a basic condensing agent or of excess ethylamine. The a-N-ät. Hylamino-caproic acid (2-chloro-6-methyl-anilide) is a colorless, acid-free oil. The hydrochloride of the base melts at 151-153.

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

Example: 33 parts by weight of a-bromo-caproic acid (2 ehlor-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with a-bromoeapronic acid bromide in the presence of sodium acetate, Sehmp.132 ") are in 150 Parts by weight of ethanol are suspended and 100 parts by weight of 70% aqueous ethylamine solution are added. The temperature rises slightly and a large part of the reaction mixture is dissolved. The mixture is then stirred for 4 hours at room temperature and then for a few hours at 65- 75. The whole thing is poured onto water, the aqueous solution is saturated with salt, and the oil which separates out 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. 29 parts by weight of pure α-N-ethylamino-caproic acid (2-chloro-6-methyl anilide) are obtained. The reaction with ethylamine can also take place in benzene.

PATENT CLAIM: Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-anilide), characterized in that a compound of the formula EMI1.2 in which X denotes a reactive radical which is split off during the reaction, with ethylamine. The α-N - ¯thylamino-caproic acid (2-chloro-6-methyl-anilide) obtained in this way forms a colorless, acid-soluble oil. The base hydrochloride melts at 151-153¯.

The new anilide will be used as a local anesthetic and as an intermediate product.

SUBJECT TO: Process according to claim, characterized in that an α-halo-eapronic acid (2-chloro-6-methyl-anilide) is allowed to react with ¯thylamine.