CH312690A - Process for the preparation of a basic substituted fatty acid amide - Google Patents

Process for the preparation of a basic substituted fatty acid amide

Info

Publication number
CH312690A
CH312690A CH312690DA CH312690A CH 312690 A CH312690 A CH 312690A CH 312690D A CH312690D A CH 312690DA CH 312690 A CH312690 A CH 312690A
Authority
CH
Switzerland
Prior art keywords
diethylamine
preparation
acetaminophenoxy
propyl
ether
Prior art date
Application number
Other languages
German (de)
Inventor
Hans Dr Suter
Zutter Hans
Widler Hans
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 CH312690A publication Critical patent/CH312690A/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
    • 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 basisch substituierten Fettsäureamides
Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, welehes dadurch gekennzeichnet ist, dass man eine Verbindung der Formel
EMI1.1     
 mit Diäthylamin umsetzt. Die Umsetzung kann in An-oder Abwesenheit von   Lösungs-bzw.   



  Verdünnungsmitteln und Anlagerungskatalysatoren erfolgen. Vorzugsweise wird wegen der Leichtflüchtigkeit des   Diäthylamins    unter Druek gearbeitet. Als Anlagerungskatalysatoren benützt man vorteilhaft quaternäre Ammoniumbasen, wie z. B. Trimethylbenzyl  ammoniumhydroxyd.   



   Das so erhaltene   S-Diäthylamino-propion-       säure-N- (3-o-acetamino-phenoxy-propyl-2)-    methylamid ist eine farblose, zähflüssige Masse.



  Das Pikrat der Base schmilzt bei   125-126 .   



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



   Beispiel
Ein Gemisch von 16, 5 g   Acrylsäure-N- (3-    O - acetamino - phenoxy - propyl-2) - methylamid, 22,   0 g Diäthylamin und    einigen Tropfen Tri  methyl-benzylammoniumhydroxyd    wird im Autoklaven während einigen Stunden auf   1450    erhitzt. Das überschüssige Diäthylamin wird abdestilliert, der Rüekstand in. Äther   auf-    genommen und mit 2n-Salzsäure ausgezogen.



  Der salzsaure Auszug wird gut mit   Ather    gewaschen und dann mit konzentrierter Lauge alkalisiert, wobei sich ein   61    ausscheidet, welches in Äther aufgenommen wird. Nach dem Trocknen über   Pottasche    wird der ¯ther verdampft und der Rüekstand im Hochvakuum getrocknet. Man gewinnt so das   fl-    Diäthylamino-propionsäure-N-   (3-o-acetamino-    phenoxy-propyl-2)-methylamid als farblose zähflüssige Masse. Das Pikrat der Base schmilzt bei   125-126 .     



   PATENTANSPRUCH
Verfahren zur Herstellung eines basisch substituierten   Fettsäureamides,    dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.2     
 mit Diäthylamin umsetzt. Das so erhaltene   8-    Diäthylamino-propionsäure-N-   (3-o-acetamino-    phenoxy-propyl-2)-methylamid ist eine farblose, zÏhfl ssige Masse. Das Pikrat der Base schmilzt bei   125-126 .   



   Es soll als   Lokalanästhetikum und    als Zwi  schenprodukt    Verwendung finden. 

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





  



  Process for the preparation of a 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, which is characterized in that a compound of the formula
EMI1.1
 Reacts with diethylamine. The implementation can in the presence or absence of solution or.



  Diluents and addition catalysts take place. Because of the volatility of diethylamine, it is preferable to work under pressure. As addition catalysts, it is advantageous to use quaternary ammonium bases, such as. B. trimethylbenzyl ammonium hydroxide.



   The S-diethylamino-propionic acid-N- (3-o-acetaminophenoxy-propyl-2) -methylamide obtained in this way is a colorless, viscous mass.



  The picrate of the base melts at 125-126.



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



   example
A mixture of 16.5 g of acrylic acid-N- (3-O-acetaminophenoxy-propyl-2) -methylamide, 22.0 g of diethylamine and a few drops of tri-methylbenzylammonium hydroxide is heated to 1450 in the autoclave for a few hours. The excess diethylamine is distilled off, the residue is taken up in ether and extracted with 2N hydrochloric acid.



  The hydrochloric acid extract is washed well with ether and then made alkaline with concentrated lye, whereupon a 61 is precipitated which is taken up in ether. After drying over potash, the ether is evaporated and the residue is dried in a high vacuum. The fl-diethylamino-propionic acid-N- (3-o-acetaminophenoxy-propyl-2) -methylamide is obtained as a colorless, viscous mass. The picrate of the base melts at 125-126.



   PATENT CLAIM
Process for the preparation of a basic substituted fatty acid amide, characterized in that a compound of the formula
EMI1.2
 Reacts with diethylamine. The 8-diethylamino-propionic acid-N- (3-o-acetaminophenoxy-propyl-2) -methylamide obtained in this way is a colorless, viscous mass. The picrate of the base melts at 125-126.



   It should be used as a local anesthetic and as an intermediate product.

** 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 basisch substituierten Fettsäureamides Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, welehes dadurch gekennzeichnet ist, dass man eine Verbindung der Formel EMI1.1 mit Diäthylamin umsetzt. Die Umsetzung kann in An-oder Abwesenheit von Lösungs-bzw. Process for the preparation of a 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, which is characterized in that a compound of the formula EMI1.1 Reacts with diethylamine. The implementation can in the presence or absence of solution or. Verdünnungsmitteln und Anlagerungskatalysatoren erfolgen. Vorzugsweise wird wegen der Leichtflüchtigkeit des Diäthylamins unter Druek gearbeitet. Als Anlagerungskatalysatoren benützt man vorteilhaft quaternäre Ammoniumbasen, wie z. B. Trimethylbenzyl ammoniumhydroxyd. Diluents and addition catalysts take place. Because of the volatility of diethylamine, it is preferable to work under pressure. As addition catalysts, it is advantageous to use quaternary ammonium bases, such as. B. trimethylbenzyl ammonium hydroxide. Das so erhaltene S-Diäthylamino-propion- säure-N- (3-o-acetamino-phenoxy-propyl-2)- methylamid ist eine farblose, zähflüssige Masse. The S-diethylamino-propionic acid-N- (3-o-acetaminophenoxy-propyl-2) -methylamide obtained in this way is a colorless, viscous mass. Das Pikrat der Base schmilzt bei 125-126 . The picrate of the base melts at 125-126. Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden. The new amide will be used as a local anesthetic and as an intermediate for the production of other derivatives. Beispiel Ein Gemisch von 16, 5 g Acrylsäure-N- (3- O - acetamino - phenoxy - propyl-2) - methylamid, 22, 0 g Diäthylamin und einigen Tropfen Tri methyl-benzylammoniumhydroxyd wird im Autoklaven während einigen Stunden auf 1450 erhitzt. Das überschüssige Diäthylamin wird abdestilliert, der Rüekstand in. Äther auf- genommen und mit 2n-Salzsäure ausgezogen. example A mixture of 16.5 g of acrylic acid-N- (3-O-acetaminophenoxy-propyl-2) -methylamide, 22.0 g of diethylamine and a few drops of tri-methylbenzylammonium hydroxide is heated to 1450 in the autoclave for a few hours. The excess diethylamine is distilled off, the residue is taken up in ether and extracted with 2N hydrochloric acid. Der salzsaure Auszug wird gut mit Ather gewaschen und dann mit konzentrierter Lauge alkalisiert, wobei sich ein 61 ausscheidet, welches in Äther aufgenommen wird. Nach dem Trocknen über Pottasche wird der ¯ther verdampft und der Rüekstand im Hochvakuum getrocknet. Man gewinnt so das fl- Diäthylamino-propionsäure-N- (3-o-acetamino- phenoxy-propyl-2)-methylamid als farblose zähflüssige Masse. Das Pikrat der Base schmilzt bei 125-126 . The hydrochloric acid extract is washed well with ether and then made alkaline with concentrated lye, whereupon a 61 is precipitated which is taken up in ether. After drying over potash, the ether is evaporated and the residue is dried in a high vacuum. The fl-diethylamino-propionic acid-N- (3-o-acetaminophenoxy-propyl-2) -methylamide is obtained as a colorless, viscous mass. The picrate of the base melts at 125-126. PATENTANSPRUCH Verfahren zur Herstellung eines basisch substituierten Fettsäureamides, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI1.2 mit Diäthylamin umsetzt. Das so erhaltene 8- Diäthylamino-propionsäure-N- (3-o-acetamino- phenoxy-propyl-2)-methylamid ist eine farblose, zÏhfl ssige Masse. Das Pikrat der Base schmilzt bei 125-126 . PATENT CLAIM Process for the preparation of a basic substituted fatty acid amide, characterized in that a compound of the formula EMI1.2 Reacts with diethylamine. The 8-diethylamino-propionic acid-N- (3-o-acetaminophenoxy-propyl-2) -methylamide obtained in this way is a colorless, viscous mass. The picrate of the base melts at 125-126. Es soll als Lokalanästhetikum und als Zwi schenprodukt Verwendung finden. It should be used as a local anesthetic and as an intermediate product.
CH312690D 1952-06-08 1952-06-08 Process for the preparation of a basic substituted fatty acid amide CH312690A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH306512T 1952-06-08
CH312690T 1952-06-08

Publications (1)

Publication Number Publication Date
CH312690A true CH312690A (en) 1956-02-15

Family

ID=25735188

Family Applications (1)

Application Number Title Priority Date Filing Date
CH312690D CH312690A (en) 1952-06-08 1952-06-08 Process for the preparation of a basic substituted fatty acid amide

Country Status (1)

Country Link
CH (1) CH312690A (en)

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