CH311612A

CH311612A - Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).

Info

Publication number: CH311612A
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 bilclet ein Verfahren zur Herstellung eines neuen basisch   substituierten Fet$säure- (Whalegen-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 Cyclohexylamin umsetzt.



   Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austa. usch gegen den   basisehen    Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer Alkylsulfonyloxy- oder Arylsulfonyloxygruppe, bestehen. Der   Austauseh    der Gruppe X gegen den   Cyclohexylaminrest erfolgt z.    B. durch einfaches Erwärmen mit Cyclohexylamin gege  benenfalls    in Gegenwart eines basisch reagie  renden Kondensationsmittels    oder von Cyclohexylamin im Überschuss. Das Cyclohexyl  amino-acet-    (2-chlor-6-methyl-anilid) ist ein farbloses   61.    Das Hydrochlorid der Base schmilzt bei   231-233 .   



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



   Beispiel:
36 Gewichtsteile   Chloracet-      (2-chlor-6-me-       th, vl-anilid) (gewonnen dureh ITmsetzen von    2-Chlor-6-methyl-anilin mit Chloracetylchlorid in Gegenwart von Natriumacetat, Schmp. 140 bis   141 )    werden in 80 Gewichtsteilen Äthanol suspendiert und mit 50 Gewichtsteilen Cyclohexylamin   verset. zt.    Die Temperatur steigt dabei leicht an und ein grosser Teil des   Reak-    tionsgemisehes geht in   Losung.    Nun wird wÏhrend 4 Stunden bei Zimmertemperatur ge  riihrt    und dann einige Stunden bei Siedetemperatur.

   Mit Wasserdampf wird hierauf der Alkohol und das   überschüssige Cyclohexyl-    a. min abgeblasen und naeh dem Erkalten das zurückbleibende Öl in Äther aufgenommen.



  Nach dem Trocknen der ätherisehen Lösung und Verjagen des   Losungsmittels    verbleibt ein   Öl,    das durch Überführen in das Hydrochlorid gereinigt wird. Man erhält 30 Ge  wichtsteile    reines   Cyclohexylamino-acet-    (2  chlor-6-methyl-anilid).    Die Umsetzung mit   Cyelohexylamin kann auch    in Benzol stattfinden.  



   PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten   Fettsäure-      (2-halogen-6-       methyl-anilids), dadurch gekennzeiehnet, dass    man eine Verbindung der Formel
EMI1.2     
 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, 

**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 production of a new basic substituted fatty acid (Whalegen-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 cyclohexylamine.



   The radical X can be in a halogen atom or another for the Austa. usch against the basic radical suitable reactive substituents, such as. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against the cyclohexylamine radical takes place z. B. by simply heating with cyclohexylamine, if necessary, in the presence of a basic reacting condensing agent or of cyclohexylamine in excess. The cyclohexylamino-acet- (2-chloro-6-methyl-anilide) is a colorless 61. The hydrochloride of the base melts at 231-233.



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



   Example:
36 parts by weight of chloroacet- (2-chloro-6-meth, vl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with chloroacetyl chloride in the presence of sodium acetate, melting point 140 to 141) are added in 80 parts by weight Suspended ethanol and mixed with 50 parts by weight of cyclohexylamine. nt. 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 boiling temperature.

   The alcohol and the excess cyclohexyl-a are then removed with steam. min blown off and after cooling the remaining oil absorbed in ether.



  After the ethereal solution has dried and the solvent has been driven off, an oil remains which is purified by converting it into the hydrochloride. 30 parts by weight of pure cyclohexylamino-acet- (2 chloro-6-methyl-anilide) are obtained. The reaction with cyelohexylamine 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,

** 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 production of a new basic substituted fatty acid (Whalegen-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 cyclohexylamine.

The radical X can be in a halogen atom or another for the Austa. usch against the basic radical suitable reactive substituents, such as. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against the cyclohexylamine radical takes place z. B. by simply heating with cyclohexylamine, if necessary, in the presence of a basic reacting condensing agent or of cyclohexylamine in excess. The cyclohexylamino-acet- (2-chloro-6-methyl-anilide) is a colorless 61. The hydrochloride of the base melts at 231-233.

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

Example: 36 parts by weight of chloroacet- (2-chloro-6-meth, vl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with chloroacetyl chloride in the presence of sodium acetate, melting point 140 to 141) are added in 80 parts by weight Suspended ethanol and mixed with 50 parts by weight of cyclohexylamine. nt. 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 boiling temperature.

The alcohol and the excess cyclohexyl-a are then removed with steam. min blown off and after cooling the remaining oil absorbed in ether.

After the ethereal solution has dried and the solvent has been driven off, an oil remains which is purified by converting it into the hydrochloride. 30 parts by weight of pure cyclohexylamino-acet- (2 chloro-6-methyl-anilide) are obtained. The reaction with cyelohexylamine 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 which is split off during the reaction, reacts with cyclohexylamine. The cyclohexylamino-acet- (2-chloro-6-methyl-anilide) obtained in this way forms a colorless oil. The hydrochloride of the base melts at 231 to 233 ′.

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

SUBClaim: Process according to patent claim, characterized in that a halogen acet (2-chloro-6-methyl-anilide) is allowed to react with cyelohexylamine.