CH311679A - Process for the production of a new basic substituted fatty acid amide. - Google Patents

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

Info

Publication number
CH311679A
CH311679A CH311679DA CH311679A CH 311679 A CH311679 A CH 311679A CH 311679D A CH311679D A CH 311679DA CH 311679 A CH311679 A CH 311679A
Authority
CH
Switzerland
Prior art keywords
diethylamine
phenoxy
propyl
methyl
fatty acid
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Cilag
Original Assignee
Cilag Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cilag Ag filed Critical Cilag Ag
Publication of CH311679A publication Critical patent/CH311679A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  



  Verfahren zur Herstellung eines neuen basisch substituierten FettsÏureamides.



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



   Der Rest X kann in einein Halogenatom oder einem sonstigen für 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   Diäthylaminrest    erfolgt z. B. durch einfaches Erwärmen mit Diäthylamin, gegebenenfalls in Gegenwart eines basisch reagierenden Kondensationsmittels, oder von Diäthylamin im   Fberschuss.    Das   N- (1-Phenoxy-propyl-2)-N-    methyl-¯-diÏthylamino-propionamid ist ein farbloses, unter 0, 07 mm bei 140-141¯ siedendes   (il.   



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



   Beispiel :
30 g N-(1-Phenoxy-propyl-2)-N-methyl-¯  l) rom-propionamid    und 22 g Diäthylamin werden zusammen in 150 cm3 abs. Benzol 6 Stunden auf dem Wasserbad erhitzt. Das   Reak-      tionsgemisch    wird mit Wasser ausgeschüttelt und dann mit   2n-Salzsäare    ausgezogen. Darauf wird der   salzsaure Auszug mit Äther    extrahiert, unter   Eiskühlung    mit konz. Natronlauge versetzt und das ausgeschiedene Öl in Äther aufgenommen. Nach dem Trocknen der   Ätherauszüge über Pottasche    wird der Äther verdampft und der Rückstand im Hochvakuum destilliert.



   Dabei gewinnt man das unter 0, 07 mm bei   140-141     siedende   N- (1-Phenoxy-propyl-2)-    N - methyl-¯-diÏthylamino - propionamid als   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 Diäthylamin umsetzt. Das auf diese Weise erhaltene N-   (1-Phenoxy-propyl-2)-N-methyl-    ¯-diÏthylamin-propionamid bildet ein fa. rbloses, unter 0,   07 mm    bei 140-141  siedendes   Ol.   



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



   UNTERANSPRUCH :
Verfahren nach Patentanspruch, dadurch gekennzeichnet, da¯ man ein N-   (1-Phenoxy-       propyl-2)-N-methyl-ss-halogenopropionamid    mit Diäthylamin reagieren lϯt. 

**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 fatty acid amide, wel elies is characterized by the fact that a compound of the formula
EMI1.1
 in weleller X means a reactive residue which is split off during the reaction, reacts with diethylamine.



   The radical X can be converted into a halogen atom or any other 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 diethylamine residue takes place z. B. by simply heating with diethylamine, optionally in the presence of a basic condensing agent, or diethylamine in excess. The N- (1-phenoxy-propyl-2) -N-methyl-¯-dithylamino-propionamide is a colorless, boiling below 0.07 mm at 140-141¯ (il.



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



   Example:
30 g of N- (1-phenoxy-propyl-2) -N-methyl-¯ l) rom-propionamide and 22 g of diethylamine are combined in 150 cm3 of abs. Benzene heated on a water bath for 6 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 separated oil was taken up in ether. After the ether extracts have been dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.



   The N- (1-phenoxy-propyl-2) -N-methyl-¯-dithylamino-propionamide, boiling below 0.07 mm at 140-141, is obtained as a 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 diethylamine. The N- (1-phenoxy-propyl-2) -N-methyl- ¯-diÏthylamine-propionamide obtained in this way forms a fa. Blossom oil boiling below 0.07 mm at 140-141.



   The new amide is to be used as a local anÏesthetic and as an intermediate product.



   SUBClaim:
Process according to patent claim, characterized in that an N- (1-phenoxy-propyl-2) -N-methyl-ss-halogenopropionamide is allowed to react with diethylamine.

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

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. Verfahren zur Herstellung eines neuen basisch substituierten FettsÏureamides. Process for the production of a new basic substituted fatty acid amide. Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, wel elies dadureh gekennzeichnet ist, dass man eine Verbindung der Formel EMI1.1 in weleller X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Diäthylamin umsetzt. The subject of the present patent forms a process for the preparation of a new basic substituted fatty acid amide, wel elies is characterized by the fact that a compound of the formula EMI1.1 in weleller X means a reactive residue which is split off during the reaction, reacts with diethylamine. Der Rest X kann in einein Halogenatom oder einem sonstigen für 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 Diäthylaminrest erfolgt z. B. durch einfaches Erwärmen mit Diäthylamin, gegebenenfalls in Gegenwart eines basisch reagierenden Kondensationsmittels, oder von Diäthylamin im Fberschuss. Das N- (1-Phenoxy-propyl-2)-N- methyl-¯-diÏthylamino-propionamid ist ein farbloses, unter 0, 07 mm bei 140-141¯ siedendes (il. The radical X can be converted into a halogen atom or any other 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 diethylamine residue takes place z. B. by simply heating with diethylamine, optionally in the presence of a basic condensing agent, or diethylamine in excess. The N- (1-phenoxy-propyl-2) -N-methyl-¯-dithylamino-propionamide is a colorless, boiling below 0.07 mm at 140-141¯ (il. Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden. The new amide is to be used as a local anesthetic and as an intermediate for the production of other derivatives. Beispiel : 30 g N-(1-Phenoxy-propyl-2)-N-methyl-¯ l) rom-propionamid und 22 g Diäthylamin werden zusammen in 150 cm3 abs. Benzol 6 Stunden auf dem Wasserbad erhitzt. Das Reak- tionsgemisch wird mit Wasser ausgeschüttelt und dann mit 2n-Salzsäare ausgezogen. Darauf wird der salzsaure Auszug mit Äther extrahiert, unter Eiskühlung mit konz. Natronlauge versetzt und das ausgeschiedene Öl in Äther aufgenommen. Nach dem Trocknen der Ätherauszüge über Pottasche wird der Äther verdampft und der Rückstand im Hochvakuum destilliert. Example: 30 g of N- (1-phenoxy-propyl-2) -N-methyl-¯ l) rom-propionamide and 22 g of diethylamine are combined in 150 cm3 of abs. Benzene heated on a water bath for 6 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 separated oil was taken up in ether. After the ether extracts have been dried over potash, the ether is evaporated and the residue is distilled in a high vacuum. Dabei gewinnt man das unter 0, 07 mm bei 140-141 siedende N- (1-Phenoxy-propyl-2)- N - methyl-¯-diÏthylamino - propionamid als farbloses, säurelösliches Öl. The N- (1-phenoxy-propyl-2) -N-methyl-¯-dithylamino-propionamide, boiling below 0.07 mm at 140-141, is obtained as a colorless, acid-soluble oil. 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- (1-Phenoxy-propyl-2)-N-methyl- ¯-diÏthylamin-propionamid bildet ein fa. rbloses, unter 0, 07 mm bei 140-141 siedendes Ol. 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- (1-phenoxy-propyl-2) -N-methyl- ¯-diÏthylamine-propionamide obtained in this way forms a fa. Blossom oil boiling below 0.07 mm at 140-141. Das neue Amid soll als LokalanÏsthetikum und als Zwischenprodukt Verwendung finden. The new amide is to be used as a local anÏesthetic and as an intermediate product. UNTERANSPRUCH : Verfahren nach Patentanspruch, dadurch gekennzeichnet, da¯ man ein N- (1-Phenoxy- propyl-2)-N-methyl-ss-halogenopropionamid mit Diäthylamin reagieren lϯt. SUBClaim: Process according to patent claim, characterized in that an N- (1-phenoxy-propyl-2) -N-methyl-ss-halogenopropionamide is allowed to react with diethylamine.
CH311679D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311679A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311679T 1952-06-08
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311679A true CH311679A (en) 1955-11-30

Family

ID=25735412

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311679D CH311679A (en) 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide.

Country Status (1)

Country Link
CH (1) CH311679A (en)

Similar Documents

Publication Publication Date Title
CH311679A (en) Process for the production of a new basic substituted fatty acid amide.
CH311680A (en) Process for the production of a new basic substituted fatty acid amide.
CH311677A (en) Process for the production of a new basic substituted fatty acid amide.
CH311678A (en) Process for the production of a new basic substituted fatty acid amide.
CH311671A (en) Process for the production of a new basic substituted fatty acid amide.
CH311685A (en) Process for the production of a new basic substituted fatty acid amide.
CH311651A (en) Process for the production of a new basic substituted fatty acid amide.
CH311645A (en) Process for the production of a new basic substituted fatty acid amide.
CH311659A (en) Process for the production of a new basic substituted fatty acid amide.
CH311690A (en) Process for the production of a new basic substituted fatty acid amide.
CH311703A (en) Process for the production of a new basic substituted fatty acid amide.
CH311688A (en) Process for the production of a new basic substituted fatty acid amide.
CH311670A (en) Process for the production of a new basic substituted fatty acid amide.
CH311687A (en) Process for the production of a new basic substituted fatty acid amide.
CH311654A (en) Process for the production of a new basic substituted fatty acid amide.
CH311653A (en) Process for the production of a new basic substituted fatty acid amide.
CH311686A (en) Process for the production of a new basic substituted fatty acid amide.
CH311707A (en) Process for the production of a new basic substituted fatty acid amide.
CH311664A (en) Process for the production of a new basic substituted fatty acid amide.
CH311663A (en) Process for the production of a new basic substituted fatty acid amide.
CH311693A (en) Process for the production of a new basic substituted fatty acid amide.
CH311665A (en) Process for the production of a new basic substituted fatty acid amide.
CH311661A (en) Process for the production of a new basic substituted fatty acid amide.
CH311674A (en) Process for the production of a new basic substituted fatty acid amide.
CH311692A (en) Process for the production of a new basic substituted fatty acid amide.