CH312689A - 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
CH312689A
CH312689A CH312689DA CH312689A CH 312689 A CH312689 A CH 312689A CH 312689D A CH312689D A CH 312689DA CH 312689 A CH312689 A CH 312689A
Authority
CH
Switzerland
Prior art keywords
diethylamine
preparation
ether
trimethyl
propyl
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 CH312689A publication Critical patent/CH312689A/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
    • 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 basisch substituierten Fettsäureamides    CTegenstand    des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen   basiseli    substituierten Fettsäureamides, welches dadurch gekennzeichnet ist, dass man eine Verbindung der Formel
EMI1.1     
 mit Diäthylamin umsetzt. Die Umsetzung kann in An-oder Abwesenheit von Lösungsbzw. Verdünnungsmitteln und Anlagerungskatalysatoren erfolgen. Vorzugsweise wird wegen der   Leichtflüchtigkeit    des   Diäthylamins    unter Druck gearbeitet. Als Anlagerungskatalysatoren benützt man vorteilhaft quaternäre Ammoniumbasen, wie z. B. Trimethylbenzylammoniumhydroxyd.



   Das so   erhaltene, -Diathylamino-propion-      säure-N-    [3-   (2',    4',   6'-trimethyl-phenoxy)-pro-    pyl-2]-methylamid ist ein farbloses, unter 0, 02 mm bei 158-159  siedendes öl.



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



   IReispiel
Ein Gemisch von 12,   0 g Acrylsäure-N- [3-        (2', 4', 6'-trimethyl-phenoxy)-propyl-2]-methyl-    amid, 13, 0 g Diäthylamin und einigen Tropfen   Trimethyl-benzylammoniumhydroxyd    wird im Autoklaven während einigen Stunden auf   145     erhitzt. Das überschüssige Diäthylamin wird abdestilliert, der Rückstand in Äther aufgenommen und mit   2n-Salzsäure    ausgezogen. Der salzsaure Auszug wird gut mit Äther gewaschen und dann mit konzentrierter Lauge alkalisiert, wobei sich ein Öl ausscheidet, welches in Äther aufgenommen wird. Nach dem Trocknen über Pottasche wird der Äther verdampft und der Rüekstand im Hochvakuum destilliert.

   Man gewinnt so das   ss-Diäthyl-      amino-propionsäure-N-    [3-   (2',      4',      6'-trimethyl-    phenoxy)-propyl-2]-methylamid als farbloses   Öl,    welches unter 0, 02 mm bei   158-159     siedet.  



   PATENTANSPRUCH
Verfahren zur Herstellung eines basisch substituierten   Fettsäureamides,    dadurch gekennzeichnet, dass man eine Verbindung der Formel 

**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 is 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. Trimethylbenzylammonium hydroxide.



   The -diethylamino-propionic acid-N- [3- (2 ', 4', 6'-trimethyl-phenoxy) -propyl-2] -methylamide obtained in this way is a colorless, below 0.02 mm at 158 -159 boiling oil.



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



   I example
A mixture of 12.0 g of acrylic acid-N- [3- (2 ', 4', 6'-trimethyl-phenoxy) -propyl-2] -methyl amide, 13.0 g of diethylamine and a few drops of trimethyl-benzylammonium hydroxide is used heated to 145 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 alkalized with concentrated lye, an oil separating out, which is absorbed in ether. After drying over potash, the ether is evaporated and the residue is distilled in a high vacuum.

   The β-diethylamino-propionic acid-N- [3- (2 ', 4', 6'-trimethylphenoxy) propyl-2] methylamide is obtained as a colorless oil, which is below 0.02 mm at 158 -159 boils.



   PATENT CLAIM
Process for the preparation of a basic substituted fatty acid amide, characterized in that a compound of the formula

** 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 CTegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basiseli substituierten Fettsäureamides, welches dadurch gekennzeichnet ist, dass man eine Verbindung der Formel EMI1.1 mit Diäthylamin umsetzt. Die Umsetzung kann in An-oder Abwesenheit von Lösungsbzw. Verdünnungsmitteln und Anlagerungskatalysatoren erfolgen. Vorzugsweise wird wegen der Leichtflüchtigkeit des Diäthylamins unter Druck gearbeitet. Als Anlagerungskatalysatoren benützt man vorteilhaft quaternäre Ammoniumbasen, wie z. B. Trimethylbenzylammoniumhydroxyd. Process for the preparation of a 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 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. Trimethylbenzylammonium hydroxide. Das so erhaltene, -Diathylamino-propion- säure-N- [3- (2', 4', 6'-trimethyl-phenoxy)-pro- pyl-2]-methylamid ist ein farbloses, unter 0, 02 mm bei 158-159 siedendes öl. The -diethylamino-propionic acid-N- [3- (2 ', 4', 6'-trimethyl-phenoxy) -propyl-2] -methylamide obtained in this way is a colorless, below 0.02 mm at 158 -159 boiling oil. 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. IReispiel Ein Gemisch von 12, 0 g Acrylsäure-N- [3- (2', 4', 6'-trimethyl-phenoxy)-propyl-2]-methyl- amid, 13, 0 g Diäthylamin und einigen Tropfen Trimethyl-benzylammoniumhydroxyd wird im Autoklaven während einigen Stunden auf 145 erhitzt. Das überschüssige Diäthylamin wird abdestilliert, der Rückstand in Äther aufgenommen und mit 2n-Salzsäure ausgezogen. Der salzsaure Auszug wird gut mit Äther gewaschen und dann mit konzentrierter Lauge alkalisiert, wobei sich ein Öl ausscheidet, welches in Äther aufgenommen wird. Nach dem Trocknen über Pottasche wird der Äther verdampft und der Rüekstand im Hochvakuum destilliert. I example A mixture of 12.0 g of acrylic acid-N- [3- (2 ', 4', 6'-trimethyl-phenoxy) -propyl-2] -methyl amide, 13.0 g of diethylamine and a few drops of trimethyl-benzylammonium hydroxide is used heated to 145 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 alkalized with concentrated lye, an oil separating out, which is absorbed in ether. After drying over potash, the ether is evaporated and the residue is distilled in a high vacuum. Man gewinnt so das ss-Diäthyl- amino-propionsäure-N- [3- (2', 4', 6'-trimethyl- phenoxy)-propyl-2]-methylamid als farbloses Öl, welches unter 0, 02 mm bei 158-159 siedet. The β-diethylamino-propionic acid-N- [3- (2 ', 4', 6'-trimethylphenoxy) propyl-2] methylamide is obtained as a colorless oil, which is below 0.02 mm at 158 -159 boils. PATENTANSPRUCH Verfahren zur Herstellung eines basisch substituierten Fettsäureamides, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI2.1 mit Diäthylamin umsetzt. Das so erhaltene ss-Diäthylamino-propionsäure-N- [3- (2', 4', 6'trimethyl-phenoxy)-propyl-2]-methylamid ist ein farbloses, unter 0, 02 mm bei 158-159 siedendes öl. Es soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. PATENT CLAIM Process for the preparation of a basic substituted fatty acid amide, characterized in that a compound of the formula EMI2.1 Reacts with diethylamine. The β-diethylamino-propionic acid-N- [3- (2 ', 4', 6'-trimethyl-phenoxy) -propyl-2] -methylamide obtained in this way is a colorless oil which boils below 0.02 mm at 158-159. It is said to be used as a local anesthetic and as an intermediate product.
CH312689D 1952-06-08 1952-06-08 Process for the preparation of a basic substituted fatty acid amide CH312689A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH312689T 1952-06-08
CH306512T 1952-06-08

Publications (1)

Publication Number Publication Date
CH312689A true CH312689A (en) 1956-02-15

Family

ID=25735187

Family Applications (1)

Application Number Title Priority Date Filing Date
CH312689D CH312689A (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) CH312689A (en)

Similar Documents

Publication Publication Date Title
CH312689A (en) Process for the preparation of a basic substituted fatty acid amide
CH312688A (en) Process for the preparation of a basic substituted fatty acid amide
CH312687A (en) Process for the preparation of a basic substituted fatty acid amide
CH312690A (en) Process for the preparation of a basic substituted fatty acid amide
CH311657A (en) Process for the production of a new basic substituted fatty acid amide.
CH311647A (en) Process for the production of a new basic substituted fatty acid amide.
CH311662A (en) Process for the production of a new basic substituted fatty acid amide.
CH311582A (en) Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide).
CH311645A (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.
CH311671A (en) Process for the production of a new basic substituted fatty acid amide.
CH311655A (en) Process for the production of a new basic substituted fatty acid amide.
CH311679A (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.
CH311687A (en) Process for the production of a new basic substituted fatty acid amide.
CH311652A (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.
CH311678A (en) Process for the production of a new basic substituted fatty acid amide.
CH311649A (en) Process for the production of a new basic substituted fatty acid amide.
CH311660A (en) Process for the production of a new basic substituted fatty acid amide.
CH311656A (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.
CH311675A (en) Process for the production of a new basic substituted fatty acid amide.
CH311667A (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.