CH311634A

CH311634A - Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).

Info

Publication number: CH311634A
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

  

  



  Verfahren zur Herstellung eines neuen basisch substituierten FettsÏure   (2-halogen-6-methyl-anilids).   



   Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch   substituierten Fettsäure- (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 n-Propylamin umsetzt.



   Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austausch gegen den basisehen   Rest geeigneten reaktionsfähi-    gen Substituenten, wie z. B. einer Alkyl  sulfonyloxy-oder Arylsulfonyloxygruppe,    bestehen. Der   Austauseh    der Gruppe X gegen   dell n-Propylaminrest    erfolgt z. B. durch einfaches Erwärmen mit n-Propylamin gegebenenfalls in Gegenwart eines basisch reagierenden Kondensationsmittels oder von n-Pro  pylamin im Überschuss.    Das a-N-n-Propyl  amino-buttersäure- (2-chlor-6-methyl-anilid    ist ein   Öl,    das nach einiger Zeit zu farblosen   Kri-    stallen erstarrt. Das Hydroehlorid der Base   schmilzt bei 169-172 .   



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



   Beispiel:
40 Gewichtsteile a-Brombuttersäure- (2chlor-6-inethylanilid) (gewonnen durch Umsetzen von 2-Chlor-6-methylanilin mit a-Brombuttersäurebromid in Gegenwart von Natriumacetat, Schmp.   162-164 )    werden in 70 Gewichtsteilen   Xthanol    suspendiert und mit 36 Gewichtsteilen n-Propylamin versetzt. Die Temperatur steigt dabei leicht an, und ein grosser Teil des   Reaktionsgemisehes    geht in   Losung.    Nun wird während 4 Stunden bei Zimmertemperatur   gerwhrt lmd    dann einige Stunden bei   65-75 .    Das Ganze wird auf Wasser gegossen und das überstehende öl in Äther aufgenommen.

   Nach dem Trocknen der ätherischen Lösung und Verjagen des   Lösungs-    mittels verbleibt ein   öl,    das durch Vakuumdestillation gereinigt wird. Man erhält 45 Gewichtsteile reines a-N-n-Propylamino-buttersaure-   (2-ehlor-6-methyl-anilid).    Die   Umset-    zung mit n-Propylamin 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 is a process for the preparation of a new basic substituted fatty acid (2-halo-6-methyl-anilide), which is characterized in that a compound of the formula
EMI1.1
 in which X is a reactive radical which is split off during the reaction, reacts with n-propylamine.



   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 alkyl sulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against dell n-Propylaminerest takes place z. B. by simply heating with n-propylamine, optionally in the presence of a basic condensing agent or n-propylamine in excess. The a-N-n-propylamino-butyric acid- (2-chloro-6-methyl-anilide is an oil which solidifies to colorless crystals after a while. The hydrochloride of the base melts at 169-172.



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



   Example:
40 parts by weight of α-bromobutyric acid (2chlor-6-ynethylanilide) (obtained by reacting 2-chloro-6-methylaniline with α-bromobutyric acid bromide in the presence of sodium acetate, melting point 162-164) are suspended in 70 parts by weight of ethanol and 36 parts by weight n-Propylamine added. The temperature rises slightly, and a large part of the reaction mixture goes into solution. It is stirred for 4 hours at room temperature and then for a few hours at 65-75. The whole is poured onto water and the supernatant oil is taken up in ether.

   After the ethereal solution has dried and the solvent has been driven off, an oil remains that is purified by vacuum distillation. 45 parts by weight of pure α-N-n-propylamino-butyric acid (2-chloro-6-methyl-anilide) are obtained. The reaction with n-propylamine 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 is a process for the preparation of a new basic substituted fatty acid (2-halo-6-methyl-anilide), which is characterized in that a compound of the formula EMI1.1 in which X is a reactive radical which is split off during the reaction, reacts with n-propylamine.

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 alkyl sulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against dell n-Propylaminerest takes place z. B. by simply heating with n-propylamine, optionally in the presence of a basic condensing agent or n-propylamine in excess. The a-N-n-propylamino-butyric acid- (2-chloro-6-methyl-anilide is an oil which solidifies to colorless crystals after a while. The hydrochloride of the base melts at 169-172.

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

Example: 40 parts by weight of α-bromobutyric acid (2chlor-6-ynethylanilide) (obtained by reacting 2-chloro-6-methylaniline with α-bromobutyric acid bromide in the presence of sodium acetate, melting point 162-164) are suspended in 70 parts by weight of ethanol and 36 parts by weight n-Propylamine added. The temperature rises slightly, and a large part of the reaction mixture goes into solution. It is stirred for 4 hours at room temperature and then for a few hours at 65-75. The whole is poured onto water and the supernatant oil is taken up in ether.

After the ethereal solution has dried and the solvent has been driven off, an oil remains that is purified by vacuum distillation. 45 parts by weight of pure α-N-n-propylamino-butyric acid (2-chloro-6-methyl-anilide) are obtained. The reaction with n-propylamine 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 is a reactive radical that is split off during the reaction, reacts with n-propylamine. The a-N-n-propylaminobutyric acid (2-chloro-6-methyl-anilide) obtained in this way forms an oil which solidifies to colorless crystals after a while. The base hydrochloride melts at 169170.

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

SUBClaim: Method according to patent claim, characterized in that one uses an α-halogen butter. acid (2-chol-6-methyl-anilide) reacts with n-propyl amine.