CH311676A

CH311676A - Process for the production of a new basic substituted fatty acid amide.

Info

Publication number: CH311676A
Authority: CH
Inventors: Aktiengesellschaft Cilag
Original assignee: Cilag Ag
Priority date: 1952-06-08
Filing date: 1952-06-08
Publication date: 1955-11-30

Description

  

  



  Verfahren zur Herstellung eines neuen basisch substituierten FettsÏureamides.



   Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen   basisch substituierten Fet. tsäurea. mides,    wel  c-lies    dadureh gekennzeichnet ist, dass man eine Verbindung der Formel
EMI1.1     
 in weleher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Diäthylamin umsetzt.



   Der Rest X kann in einem Halogenatom oder einem sonstigen f r den Austausch gegen den   basisehen    Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer Alkylsul  fonyloxy-oder Arylsulfonyloxygruppe,    bestehen. Der Austausch der Gruppe X gegen den Diä. thylaminrest erfolgt z. B. durch einfaches Erwärmen mit Diäthylamin, gegebenenfalls in Gegenwart eines basisch reagierenden Kondensationsmittels, oder von Diäthylamin   im tTber-      sehuss. Das N-    [2-   (3'-Methyl-phenoxy)-athyl-1]-      N-methyl-diäthylaminoacetamid    ist ein farbloses, unter 0, 04mm bei   140-141     siedendes   61.   



   Das neue Amid soll als   Lokalanästhetikum    und als Zwischenprodukt zur Herstellung wei  Rerel Oerivate Verwendung    finden.



   Beispiel :
24, 2 g   N- [2- (3'-Methyl-phenoxy)-athyl-l]-    N-methyl-ehloraeetamid und 20 g Diäthylamin werden zusammen in 150   em3    abs. Benzol 6 Stunden auf dem Wasserbad erhitzt. Das   Re-      aktionsgemisch    wird mit Wasser   ausgeschüt-    telt und dann mit 2n-Salzsäure ausgezogen.



  Darauf wird der salzsaure Auszug mit Äther extrahiert, unter   Eiskühhmg    mit konz. Natronlauge versetzt und das   ausgesehiedene    Íl in ¯ther aufgenommen. Nach dem Trocknen der   Ätherauszüge    über   Pottasche    wird der Äther verdampft und der Rüekstand im Hochvakuum destilliert.



   Dabei gewinnt man das unter 0, 04 mm bei 140-141¯ siedende N- [2-   (3'-Methyl-phenoxy)-    Ïthyl - 1] - N- methyl - diÏthylaminoacetamid als farbloses,   säurelösliches      61.     



   PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.2     
 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Diäthylamin umsetzt. Das auf diese Weise erhaltene N- [2- (3'-Methyl-phenoxy)-äthyl-1]  N-methyl-diäthylaminoacetamid    bildet ein farbloses, unter 0, 04mm bei   140-141     siedendes   61.   



   Das neue Amid soll als   Lokalanästhetikum    und als Zwischenprodukt Verwendung finden.



   UNTERANSPRUCH :
Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein   N- [2- (3'-Methyl-       phenoxy)-äthyl-1]-N-methyl-halogenacetamid    mit Diäthylamin reagieren lÏ¯t. 

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





  



  Process for the production of a new basic substituted fatty acid amide.



   The subject of the present patent is a process for the production of a new basic substituted fat. acid a. mides, wel c-lies dadureh is characterized as being a compound of the formula
EMI1.1
 in which X is a reactive radical that is split off during the reaction, reacts with diethylamine.



   The radical X can be in a halogen atom or any other reactive substituent suitable for replacement with the basic radical, such as e.g. B. an alkyl sulfonyloxy or aryl sulfonyloxy group exist. The exchange of group X for the diet. thylaminrest takes place z. B. by simply heating with diethylamine, optionally in the presence of a basic condensing agent, or diethylamine in excess. The N- [2- (3'-methyl-phenoxy) -ethyl-1] - N-methyl-diethylaminoacetamide is a colorless 61, boiling below 0.04 mm at 140-141.



   The new amide is to be used as a local anesthetic and as an intermediate product for the manufacture of white derivatives.



   Example:
24, 2 g of N- [2- (3'-methyl-phenoxy) -ethyl-1] - N-methyl-ehloraeetamid and 20 g of diethylamine are dissolved together in 150 em3 abs. Benzene heated on a water bath for 6 hours. The reaction mixture is extracted by shaking with water and then extracted with 2N hydrochloric acid.



  Then the hydrochloric acid extract is extracted with ether, under ice cream with conc. Sodium hydroxide solution was added and the separated oil was taken up in ¯ther. After the ether extracts have dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.



   The N- [2- (3'-methylphenoxy) - ethyl - 1] - N-methyl - diethylaminoacetamide, boiling below 0.04 mm at 140-141¯, is obtained as colorless, acid-soluble 61.



   PATENT CLAIM:
Process for the preparation of a new basic substituted fatty acid amide, characterized in that a compound of the formula
EMI1.2
 in which X is a reactive radical which is split off during the reaction, is reacted with diethylamine. The N- [2- (3'-methyl-phenoxy) -ethyl-1] N-methyl-diethylaminoacetamide obtained in this way forms a colorless 61 boiling below 0.04 mm at 140-141.



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



   SUBClaim:
Process according to patent claim, characterized in that an N- [2- (3'-methylphenoxy) ethyl-1] -N-methyl-haloacetamide is allowed to react with diethylamine.

** 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 amide.

The subject of the present patent is a process for the production of a new basic substituted fat. acid a. mides, wel c-lies dadureh is characterized as being a compound of the formula EMI1.1 in which X is a reactive radical that is split off during the reaction, reacts with diethylamine.

The radical X can be in a halogen atom or any other reactive substituent suitable for replacement with the basic radical, such as e.g. B. an alkyl sulfonyloxy or aryl sulfonyloxy group exist. The exchange of group X for the diet. thylaminrest takes place z. B. by simply heating with diethylamine, optionally in the presence of a basic condensing agent, or diethylamine in excess. The N- [2- (3'-methyl-phenoxy) -ethyl-1] - N-methyl-diethylaminoacetamide is a colorless 61, boiling below 0.04 mm at 140-141.

The new amide is to be used as a local anesthetic and as an intermediate product for the manufacture of white derivatives.

Example: 24, 2 g of N- [2- (3'-methyl-phenoxy) -ethyl-1] - N-methyl-ehloraeetamid and 20 g of diethylamine are dissolved together in 150 em3 abs. Benzene heated on a water bath for 6 hours. The reaction mixture is extracted by shaking with water and then extracted with 2N hydrochloric acid.

Then the hydrochloric acid extract is extracted with ether, under ice cream with conc. Sodium hydroxide solution was added and the separated oil was taken up in ¯ther. After the ether extracts have dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.

The N- [2- (3'-methylphenoxy) - ethyl - 1] - N-methyl - diethylaminoacetamide, boiling below 0.04 mm at 140-141¯, is obtained as colorless, acid-soluble 61.

PATENT CLAIM: Process for the preparation of a new basic substituted fatty acid amide, characterized in that a compound of the formula EMI1.2 in which X is a reactive radical which is split off during the reaction, is reacted with diethylamine. The N- [2- (3'-methyl-phenoxy) -ethyl-1] N-methyl-diethylaminoacetamide obtained in this way forms a colorless 61 boiling below 0.04 mm at 140-141.

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

SUBClaim: Process according to patent claim, characterized in that an N- [2- (3'-methylphenoxy) ethyl-1] -N-methyl-haloacetamide is allowed to react with diethylamine.