CH311562A - 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
- CH311562A CH311562A CH311562DA CH311562A CH 311562 A CH311562 A CH 311562A CH 311562D A CH311562D A CH 311562DA CH 311562 A CH311562 A CH 311562A
- Authority
- CH
- Switzerland
- Prior art keywords
- fatty acid
- production
- acid amide
- substituted fatty
- new basic
- 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
-
- 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)
- Hydrogenated Pyridines (AREA)
Description
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, wel ches dadurch gekennzeichnet ist, dass man auf eine Verbindung der Formel
EMI0001.0008
eine Verbindung der Formel
EMI0001.0009
in welchen Formeln X und Y reaktionsfähige, bei der Reaktion sich abspaltende Reste be deuten, einwirken lässt.
Als Verbindungen der Formel I kommen für einen Umsatz beispielsweise in Frage: Das freie Amin (Y = H), aber auch dessen Salze, wie beispielsweise das Hydrochlorid oder das Sulfat.
Als Verbindungen der Formel II kommen beispielsweise in Frage: 2,6-Dimethyl-piperi- dino-essigsäure selbst und ihre reaktionsfähi gen funktionellen Derivate wie ihre Haloge- nide, ihre Ester, ihre Anhydride, beispiels weise die reinen und auch die gemischten Anhydride mit Phosphorsäure, Schwefelsäure und Kohlensäure usf.
Man kann beispielsweise N-(2-Phenoxy- äthyl-1)-N-methyl-amin oder auch ein Salz desselben in Gegenwart eines für diese Zwecke geeigneten wasserabspaltenden Mittels wie Phosphorpentoxyd, Phosphoroxychlorid usf. mit 2,6-Dimethyl-piperidino-essigsäure behan deln.
Weiter kann man auch N-(2-Phenoxy- äthyl-1)-N-methyl-amin bzw. ein Salz dessel ben mit einem 2,6-Dimethyl-piperidino-essig- säurehalogenid (bzw. einem Salz eines sol chen) oder einem Anhydrid zur Reaktion bringen.
Es ist weiterhin auch möglich, N-(2-Phen- oxy-äthyl-1)-N-methyl-amin mit einem 2,6-Di- methyl - piperidino - essigsäureester, vorzugs weise einem Arylester, bei erhöhter Tempera tur zu acylieren.
Das auf diese Weise erhaltene N-(2-Phen- oxy-äthyl-1) -N-methyl - 2',6'- dimethyl- piperi- dino-acetamid bildet ein farbloses, unter 0,06 mm bei 157-158 siedendes öl.
Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt mir Herstellung wei terer Derivate Verwendung finden.
<I>Beispiel:</I> 15,2g N-(2-Phenoxy-äthyl-1)-N-methyl- amin in Benzol werden mit einer Mischung von 22,6 g 2,6-Dimethyl-piperidino-essigsäure- chlorid-hydrochlorid und 20 g Triäthylamin erwärmt.
Anschliessend wird das gebildete Triäthylaminhydrochlorid durch Ausschütteln mit Wasser entfernt, die Benzollösung nach dem Trocknen verdampft und der Rückstand im IIochvakuum destilliert. Man erhält so in guter Ausbeute das N-(2-Phenoxy-äthyl-1)-N- methyl-2',6'-dimethyl-piperidino-acetamid, wel ches ein unter 0,06 mm bei 157-158 sieden des farbloses Öl darstellt.
Die Reaktion kann auch ohne Verdün- nungs- und Kondensationsmittel durchgeführt werden, indem man beispielsweise das N-(2 Phenoxy-äthyl-1)-N-methyl-amin mit 2,6-Di- inethyl-piperidino-essigsäure - chlorid-hydro- ehlorid trocken erhitzt, anschliessend die Re aktionsmasse mit Wasser verdünnt und in üblicher Weise aufarbeitet.
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, wel Ches is characterized in that one is based on a compound of the formula
EMI0001.0008
a compound of the formula
EMI0001.0009
in which formulas X and Y are reactive residues that are split off during the reaction.
Compounds of the formula I that can be used for conversion are, for example: The free amine (Y = H), but also its salts, such as the hydrochloride or the sulfate, for example.
Examples of possible compounds of the formula II are: 2,6-dimethyl-piperidino-acetic acid itself and its reactive functional derivatives such as its halides, its esters, their anhydrides, for example the pure and also the mixed anhydrides Phosphoric acid, sulfuric acid and carbonic acid etc.
For example, N- (2-phenoxyethyl-1) -N-methyl-amine or a salt thereof in the presence of a dehydrating agent suitable for this purpose such as phosphorus pentoxide, phosphorus oxychloride, etc. with 2,6-dimethylpiperidinoacetic acid to treat.
You can also use N- (2-phenoxy-ethyl-1) -N-methyl-amine or a salt thereof with a 2,6-dimethyl-piperidino-acetic acid halide (or a salt of such) or bring an anhydride to reaction.
It is also possible to acylate N- (2-phenoxy-ethyl-1) -N-methyl-amine with a 2,6-dimethyl - piperidino - acetic acid ester, preferably an aryl ester, at an elevated temperature .
The N- (2-phenoxy-ethyl-1) -N-methyl-2 ', 6'-dimethylpiperidino-acetamide obtained in this way forms a colorless one, boiling below 0.06 mm at 157-158 oil.
The new amide is to be used as a local anesthetic and as an intermediate product for the manufacture of further derivatives.
<I> Example: </I> 15.2 g of N- (2-phenoxy-ethyl-1) -N-methyl-amine in benzene are mixed with a mixture of 22.6 g of 2,6-dimethyl-piperidino-acetic acid chloride hydrochloride and 20 g of triethylamine heated.
The triethylamine hydrochloride formed is then removed by shaking with water, the benzene solution is evaporated after drying and the residue is distilled in a high vacuum. The N- (2-phenoxy-ethyl-1) -N-methyl-2 ', 6'-dimethyl-piperidino-acetamide, which boils below 0.06 mm at 157-158 of the colorless, is obtained in good yield Represents oil.
The reaction can also be carried out without diluents and condensation agents, for example by adding the N- (2-phenoxy-ethyl-1) -N-methyl-amine with 2,6-dimethyl-piperidino-acetic acid - chloride-hydro - Ehlorid heated dry, then the Re action mass diluted with water and worked up in the usual way.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH311562T | 1952-06-08 | ||
CH306201T | 1955-03-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH311562A true CH311562A (en) | 1955-11-30 |
Family
ID=25735089
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH311562D CH311562A (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) | CH311562A (en) |
-
1952
- 1952-06-08 CH CH311562D patent/CH311562A/en unknown
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