CH328670A - 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 amideInfo
- Publication number
- CH328670A CH328670A CH328670DA CH328670A CH 328670 A CH328670 A CH 328670A CH 328670D A CH328670D A CH 328670DA CH 328670 A CH328670 A CH 328670A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- fatty acid
- acid amide
- production
- substituted fatty
- Prior art date
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
- C07D295/145—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 with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—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 with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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 Fettsäureamides Gegenstand des vorliegenden Patentes bil det ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, wel ches dadurch gekennzeichnet ist, dass man eine Verbindung der Formel
EMI0001.0009
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Pyrrolidin umsetzt.
Der Rest X kann, in einem Halogenatom oder einem sonstigen für den Austausch ge gen den basischen Rest geeigneten reaktions- fähigen Substituenten, wie zum Beispiel einer AIkyls@ilfonyloxy=oder Arylsulfonyloxygruppe bestehen.
Der Austausch der Gruppe X gegen den Pyrrolidinrest erfolgt zum Beispiel durch einfaches Erwärmen mit Pyrrolidin, gege benenfalls in Gegenwart eines basisch reagie renden Kondensationsmittels oder von Pyrroli- din im Überschuss. Das N- [1- (3' - Butoxy- phenoxy)-äthyl-'2]-N methyl-pyrrölidino,.acet- amid ist .ein, farbloses, unter 0;
06 mm bei 185 bis 186 siedendes Mi. Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung weiterer Derivate Verwen- dung finden. <I>Beispiel</I> 30, g N-[1-(W-cButoxy-phenoxy)-äthyl2]- N-methyl-chloracetamid und 11 g Pyrroldin werden zusammen in 50 em3 abs. Benzol 6 iStunden auf dem Wasserbad erhitzt.
Das Reaktionsgemisch wird mit Wasser ausgeschüt telt und dann mit 2n-SaflzsäLtre ausgezogen. Darauf wird der salzsaure Auszug mit Äther extrahiert,
unter Eiskühlung mit konzentrier ter Natronlauge versetzt und das ausgeschie- dene Öl in Äther aufgenommen. Nach dein Trocknen der Ätherauszüge über Pottasche wird der Äther verdampft und der Rückstand im Hochvakuum destilliert.
Dabei gewinnt man das unter 0,0'6 mm bei 185=186 siedende N-[1 ('3'-Butoxy-phenoxy)- äthyl2] - N-methyl - pyrroiidino - acetamid als farbloses, säureläsliches iöl.
Process for the preparation of a new basic substituted fatty acid amide 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
EMI0001.0009
in which X is a reactive radical which is split off during the reaction, reacts with pyrrolidine.
The radical X can consist of a halogen atom or some other reactive substituent suitable for exchange with the basic radical, such as an alkyls @ ilfonyloxy = or arylsulfonyloxy group.
The group X is exchanged for the pyrrolidine radical, for example, by simply heating with pyrrolidine, if necessary in the presence of a basic reacting condensing agent or an excess of pyrrolidine. The N- [1- (3 '- butoxyphenoxy) ethyl-'2] -N methyl-pyrrölidino, .acetamide is .ein, colorless, below 0;
06 mm at 185 to 186 boiling Mi. The new amide is to be used as a local anesthetic and as an intermediate product for the production of further derivatives. <I> Example </I> 30 g of N- [1- (W-cButoxy-phenoxy) -ethyl2] - N-methyl-chloroacetamide and 11 g of pyrroldine are mixed together in 50 em3 abs. Benzene heated on a water bath for 6 hours.
The reaction mixture is extracted by shaking with water and then extracted with 2N safflower acid. The hydrochloric acid extract is then extracted with ether,
concentrated sodium hydroxide solution was added while cooling with ice and the separated oil was taken up in ether. After drying the ether extracts over potash, the ether is evaporated and the residue is distilled in a high vacuum.
The N- [1 ('3'-butoxyphenoxy) -ethyl2] -N-methyl-pyrroidino-acetamide boiling below 0.0'6 mm at 185 = 186 is obtained as a colorless, acid-soluble oil.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH328670T | 1952-06-08 | ||
| CH307799T | 1952-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH328670A true CH328670A (en) | 1958-03-15 |
Family
ID=25735446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH328670D CH328670A (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) | CH328670A (en) |
-
1952
- 1952-06-08 CH CH328670D patent/CH328670A/en unknown
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