CH311680A

CH311680A - Process for the production of a new basic substituted fatty acid amide.

Info

Publication number: CH311680A
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 FettsÏureamides, welches dadurch gekennzeichnet ist,   dans man    eine Verbindung der Formel
EMI1.1     
 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit   N-Butylamin    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   Alkylsul-      fonyloxy-oder Arylsulfonyloxygruppe,    bestehen. Der Austausch der Gruppe X gegen den   Butylaminrest    erfolgt z. B. durch einfaches Erwärmen mit Butylamin, gegebenenfalls in Gegenwart eines basiseh reagierenden Kondensationsmittels, oder von   Butylamin im Über-    schuss.   Das N- (2-Phenoxy-äthvl-1)-N-methyl-    n-butylamino-acetamid ist ein farbloses, unter 0, 05 mm bei 168-169¯ siedendes   61.   



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



   Beispiel :
22, 8 g N-   (2-Phenoxy-äthyl-1)-N-methyl-    chloracetamid und 29 g n-Butylamin werden zusammen in 150 cm3 abs. Benzol 5 Stunden auf dem Wasserbad erhitzt. Das   Reaktions-    gemisch wird mit Wasser ausgeschüttelt und dann mit   2n-Salzsäure ausgezogen. Darauf    wird der   salzsaure    Auszug mit Äther extrahiert, unter Eiskühlung mit konz. Natronlauge versetzt und das ausgeschiedene Íl in Äther aufgenommen. Nach dem Trocknen der   Äther-    auszüge über   Pottasche    wird der Äther verdampft und der Rüekstand im Hochvakuum destilliert.



   Da, bei gewinnt man das unter 0, 05 mm bei 168-169  siedende N-(2-Phenoxy-Ïthyl-1)-N  methyl-n-butylamino-acetamid    a. ls farbloses,   säurelösliches öl.     



   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   n-Butylamin    umsetzt. Das auf diese Weise erhaltene N- (2-Phenoxy-äthyl-1)-N-methyl-n  butylamino-aeetamid    bildet ein farbloses, unter 0, 05 mm bei 168-169  siedendes   Öl.   



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



   UNTERANSPRUCH :
Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein N-   (2-Phenoxy-      äthyl-1)-N-methyl-halogenoacetamid    mit n Butylamin reagieren lässt. 

**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 forms a process for the preparation of a new basic substituted FettsÏureamides, which is characterized by using a compound of the formula
EMI1.1
 in which X is a reactive radical which is split off during the reaction, is reacted with N-butylamine.



   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 alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against the butylamine residue takes place, for. B. by simply heating with butylamine, optionally in the presence of a basic reacting condensing agent, or an excess of butylamine. The N- (2-phenoxy-ether-1) -N-methyl-n-butylamino-acetamide is a colorless 61 that boils below 0.05 mm at 168-169¯.



   The new amide will be used as a local anesthetic and as an intermediate for the production of other derivatives.



   Example:
22.8 g of N- (2-phenoxy-ethyl-1) -N-methyl-chloroacetamide and 29 g of n-butylamine are dissolved together in 150 cm3 of abs. Benzene heated on a water bath for 5 hours. The reaction mixture is extracted with water and then extracted with 2N hydrochloric acid. The hydrochloric acid extract is then extracted with ether, with conc. Sodium hydroxide solution was added and the excreted oil was taken up in ether. After the ether extracts have dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.



   There, one wins the under 0.05 mm boiling at 168-169 N- (2-phenoxy-ethyl-1) -N methyl-n-butylamino-acetamide a. ls colorless, acid-soluble oil.



   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 n-butylamine. The N- (2-phenoxy-ethyl-1) -N-methyl-n-butylamino-aeetamide obtained in this way forms a colorless oil which boils at 168-169 below 0.05 mm.



   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-phenoxy-ethyl-1) -N-methyl-halogenoacetamide is allowed to react with n-butylamine.

** 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 forms a process for the preparation of a new basic substituted FettsÏureamides, which is characterized by using a compound of the formula EMI1.1 in which X is a reactive radical which is split off during the reaction, is reacted with N-butylamine.

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 alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against the butylamine residue takes place, for. B. by simply heating with butylamine, optionally in the presence of a basic reacting condensing agent, or an excess of butylamine. The N- (2-phenoxy-ether-1) -N-methyl-n-butylamino-acetamide is a colorless 61 that boils below 0.05 mm at 168-169¯.

The new amide will be used as a local anesthetic and as an intermediate for the production of other derivatives.

Example: 22.8 g of N- (2-phenoxy-ethyl-1) -N-methyl-chloroacetamide and 29 g of n-butylamine are dissolved together in 150 cm3 of abs. Benzene heated on a water bath for 5 hours. The reaction mixture is extracted with water and then extracted with 2N hydrochloric acid. The hydrochloric acid extract is then extracted with ether, with conc. Sodium hydroxide solution was added and the excreted oil was taken up in ether. After the ether extracts have dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.

There, one wins the under 0.05 mm boiling at 168-169 N- (2-phenoxy-ethyl-1) -N methyl-n-butylamino-acetamide a. ls colorless, acid-soluble oil.

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 n-butylamine. The N- (2-phenoxy-ethyl-1) -N-methyl-n-butylamino-aeetamide obtained in this way forms a colorless oil which boils at 168-169 below 0.05 mm.

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-phenoxy-ethyl-1) -N-methyl-halogenoacetamide is allowed to react with n-butylamine.