CH311655A - 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
CH311655A
CH311655A CH311655DA CH311655A CH 311655 A CH311655 A CH 311655A CH 311655D A CH311655D A CH 311655DA CH 311655 A CH311655 A CH 311655A
Authority
CH
Switzerland
Prior art keywords
diethylamine
phenoxy
propyl
dimethyl
radical
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 CH311655A publication Critical patent/CH311655A/en

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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

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

Description

  

  



  Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides.



   Gegenstand des vorliegenden Patentes   bil-    det   ein Verfahren zur Herstellung    eines neuen   basisch substituierten Fettsäureamides,    wel  rhes dadureh gekennzeichnet    ist, dass man eine Verbindung der Formel
EMI1.1     
 in welcher X einen reaktionsfähigen, während der Reaktion sieh abspaltenden Rest bedeutet, mit Diäthylamin umsetzt.



   Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austausch gegen den basisehen Rest geeigneten reaktionsfähigen Substituenten, wie z.   B.    einer Alkylsulfo   nyloxy-oder Arylsulfonvloxygruppe, bestehen.   



  Der Austausch der Gruppe X gegen den Di äthylaminorest erfolgt zum Beispiel durch einfaches Erwärmen mit Diäthylamin. gegebenenfalls in   Cegenwart eines basisch reagieren-    den Kondensationsmittels oder von Diäthy]amin im   Übersehuss.    Das   Diäthylaminoessig-       säure-N- [3- (3', 5'-dimethyl-phenoxy)-propyl-2]-      : ithylamid    ist ein farbloses, unter 0, 02 mm bei 155-156  siedendes   01.   



   Das neue Amid soll als   Lokalanästhetikum    und als Zwischenprodukt zur   Herstellmg    wei  terer Derivate Verwendung    finden.



   Beispiel :
28, 3 g Chloressigsäure-N- [3- (3',   5'-dimethyl-    phenoxy)-propyl-2]-äthylamid und 14, 9 g Di  äthylamin    werden zusammen in 200 cm3 abs.



  Benzol 2 Stunden auf dem Wasserbad erhitzt.



  Das Reaktionsgemisch wird mit Wasser ausgesehüttelt und dann mit 2n-Salzsäure ausgezogen. Darauf wird der   salzsaure    Auszug mit Äther extrahiert, unter Eiskühlung mit konz. Natronlauge   versetzt und das ausge-      schiedene    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, 02 mm bei 155-156  siedende Diäthylaminoessigsäure-N  [3-f (3', 5'-dimethyl-phenoxy)-propyl-2]-äthylamid in guter Ausbeute. Farbloses Öl, schwer löslich in Wasser, gut in organischen   Lösungs-    mitteln und in verdünnten Mineralsäuren.  



   PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen    basisch substituierten Fettsäureamides, da-    dureli gekennzeichnet, dass man eine   Verbin-    dung der Formel
EMI1.2     
 in welcher X einen reaktionsfähigen, während der Reaktion sieh abspaltenden Rest bedeutet, 

**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 preparation of a new basic substituted fatty acid amide, which is characterized by the fact that a compound of the formula
EMI1.1
 in which X denotes a reactive radical which is split off during the reaction, 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 Alkylsulfo nyloxy or Arylsulfonvloxygruppe exist.



  Group X is exchanged for the diethylamino radical, for example, by simply heating with diethylamine. possibly in the presence of an alkaline condensing agent or an excess of diethy] amine. The diethylaminoacetic acid N- [3- (3 ', 5'-dimethyl-phenoxy) -propyl-2] -: ithylamide is a colorless oil that boils below 0.02 mm at 155-156.



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



   Example:
28, 3 g of chloroacetic acid-N- [3- (3 ', 5'-dimethyl-phenoxy) -propyl-2] -ethylamide and 14, 9 g of diethylamine are combined in 200 cm3 of abs.



  Benzene heated on a water bath for 2 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 is added and the separated oil is absorbed 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 diethylaminoacetic acid N [3-f (3 ', 5'-dimethyl-phenoxy) -propyl-2] -ethylamide, boiling below 0.02 mm at 155-156, is obtained in good yield. Colorless oil, sparingly soluble in water, good in organic solvents and in dilute mineral acids.



   PATENT CLAIM:
Process for the production of a new basic substituted fatty acid amide, characterized by the fact that one is 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 (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 Fettsäureamides. Process for the production of a new basic substituted fatty acid amide. Gegenstand des vorliegenden Patentes bil- det ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, wel rhes dadureh gekennzeichnet ist, dass man eine Verbindung der Formel EMI1.1 in welcher X einen reaktionsfähigen, während der Reaktion sieh abspaltenden Rest bedeutet, mit Diäthylamin umsetzt. The subject of the present patent is a process for the preparation of a new basic substituted fatty acid amide, which is characterized by the fact that a compound of the formula EMI1.1 in which X denotes a reactive radical which is split off during the reaction, with diethylamine. Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austausch gegen den basisehen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer Alkylsulfo nyloxy-oder Arylsulfonvloxygruppe, bestehen. 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 Alkylsulfo nyloxy or Arylsulfonvloxygruppe exist. Der Austausch der Gruppe X gegen den Di äthylaminorest erfolgt zum Beispiel durch einfaches Erwärmen mit Diäthylamin. gegebenenfalls in Cegenwart eines basisch reagieren- den Kondensationsmittels oder von Diäthy]amin im Übersehuss. Das Diäthylaminoessig- säure-N- [3- (3', 5'-dimethyl-phenoxy)-propyl-2]- : ithylamid ist ein farbloses, unter 0, 02 mm bei 155-156 siedendes 01. Group X is exchanged for the diethylamino radical, for example, by simply heating with diethylamine. possibly in the presence of an alkaline condensing agent or an excess of diethy] amine. The diethylaminoacetic acid N- [3- (3 ', 5'-dimethyl-phenoxy) -propyl-2] -: ithylamide is a colorless oil that boils below 0.02 mm at 155-156. Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellmg wei terer Derivate Verwendung finden. The new amide will be used as a local anesthetic and as an intermediate for the production of further derivatives. Beispiel : 28, 3 g Chloressigsäure-N- [3- (3', 5'-dimethyl- phenoxy)-propyl-2]-äthylamid und 14, 9 g Di äthylamin werden zusammen in 200 cm3 abs. Example: 28, 3 g of chloroacetic acid-N- [3- (3 ', 5'-dimethyl-phenoxy) -propyl-2] -ethylamide and 14, 9 g of diethylamine are combined in 200 cm3 of abs. Benzol 2 Stunden auf dem Wasserbad erhitzt. Benzene heated on a water bath for 2 hours. Das Reaktionsgemisch wird mit Wasser ausgesehüttelt und dann mit 2n-Salzsäure ausgezogen. Darauf wird der salzsaure Auszug mit Äther extrahiert, unter Eiskühlung mit konz. Natronlauge versetzt und das ausge- schiedene Öl in Äther aufgenommen. Nach dem Trocknen der Ätherauszüge über Pottasche wird der Äther verdampft und der Rückstand im Hochvakuum destilliert. 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 is added and the separated oil is absorbed 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, 02 mm bei 155-156 siedende Diäthylaminoessigsäure-N [3-f (3', 5'-dimethyl-phenoxy)-propyl-2]-äthylamid in guter Ausbeute. Farbloses Öl, schwer löslich in Wasser, gut in organischen Lösungs- mitteln und in verdünnten Mineralsäuren. The diethylaminoacetic acid N [3-f (3 ', 5'-dimethyl-phenoxy) -propyl-2] -ethylamide, boiling below 0.02 mm at 155-156, is obtained in good yield. Colorless oil, sparingly soluble in water, good in organic solvents and in dilute mineral acids. PATENTANSPRUCH : Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, da- dureli gekennzeichnet, dass man eine Verbin- dung der Formel EMI1.2 in welcher X einen reaktionsfähigen, während der Reaktion sieh abspaltenden Rest bedeutet, mit Diäthylamin umsetzt. Das auf diese Weise erhaltene Diathylaminoessigsa. ure-N- [3 (3',5'-dimethyl-phenoxy)-propyl-2]-äthylamid bildet ein farbloses, unter 0, 02 mm bei 155 bis 156 siedendes Öl. PATENT CLAIM: Process for the preparation of a new basic substituted fatty acid amide, characterized by the fact that one is a compound of the formula EMI1.2 in which X denotes a reactive radical which is split off during the reaction, with diethylamine. The diethylaminoacetic acid obtained in this way. ure-N- [3 (3 ', 5'-dimethyl-phenoxy) -propyl-2] -ethylamide forms a colorless oil which boils below 0.02 mm at 155 to 156. Das neue Amid soll als Lokalanästhetikum und als Zwischenprodnkt Verwendmg finden. The new amide is said to be used as a local anesthetic and as an intermediate product. UNTERANSPRUCH : Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein Halogenessigsäure-N- [3-(3',5'-dimethyl-phenoxy)-propyl-2] äthylamid mit Diäthylamin reagieren last. SUBClaim: Process according to claim, characterized in that a haloacetic acid-N- [3- (3 ', 5'-dimethyl-phenoxy) -propyl-2] ethylamide is allowed to react with diethylamine.
CH311655D 1952-06-08 1952-06-08 Process for the production of a new basic substituted fatty acid amide. CH311655A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311655T 1952-06-08
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311655A true CH311655A (en) 1955-11-30

Family

ID=25735388

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311655D CH311655A (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) CH311655A (en)

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