CH311577A - 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
- CH311577A CH311577A CH311577DA CH311577A CH 311577 A CH311577 A CH 311577A CH 311577D A CH311577D A CH 311577DA CH 311577 A CH311577 A CH 311577A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- production
- fatty acid
- acid amide
- substituted fatty
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 4
- 239000000194 fatty acid Substances 0.000 title claims description 4
- 229930195729 fatty acid Natural products 0.000 title claims description 4
- 150000004665 fatty acids Chemical class 0.000 title claims description 4
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- IPXNXMNCBXHYLQ-UHFFFAOYSA-N 2-pyrrolidin-1-ylacetic acid Chemical compound OC(=O)CN1CCCC1 IPXNXMNCBXHYLQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000012230 colorless oil Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- QAHFOPIILNICLA-UHFFFAOYSA-N Diphenamid Chemical compound C=1C=CC=CC=1C(C(=O)N(C)C)C1=CC=CC=C1 QAHFOPIILNICLA-UHFFFAOYSA-N 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- -1 for example Chemical class 0.000 description 3
- FXEAGDBAXGKYIA-UHFFFAOYSA-N 2-pyrrolidin-1-ylacetyl chloride;hydrochloride Chemical compound Cl.ClC(=O)CN1CCCC1 FXEAGDBAXGKYIA-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen basiseh substituierten Fettsäureamides, wel- ehes dadurch gekennzeichnet ist, dass man auf eine Verbindung der Formel
EMI0001.0009
eine Verbindung der Formel
EMI0001.0010
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 (las Sulfat.
Als Verbindungen der Formel II kommen beispielsweise in Frage: Pyrrolidinoessigsäure selbst und ihre reaktionsfähigen funktionellen Derivate wie ihre Halogenide, ihre Ester, ihre Anhydride, beispielsweise die reinen und auch die gemischten Anhydride mit Phosphorsäure, Schwefelsäure und Kohlensäure usf.
Man kann beispielsweise N-[2-(3'-Methoxy- phenoxp)-äthyl-1]-amin oder auch ein Salz desselben in Gegenwart eines für diese Zwecke geeigneten wasserabspaltenden Mittels wie Phosphorpentoxyd, Phosphoroxychlorid usf. mit Pyrrolidinoessigsäure behandeln. Weiter kann man auch N-[2-(3'-Methoxy- phenoxy)-äthyl-1]-amin bzw. ein Salz dessel ben mit einem Pyrrolidinoessigsäurehalogenid (bzw. einem Salz eines solchen) oder einem Anhydrid zur Reaktion bringen.
Es ist weiterhin auch möglich, N-[2-(3'- Methoxy-phenoxy)-äthyl-1]-amin mit einem Pyrrolidinoessigsäureester, vorzugsweise einem Arylester, bei erhöhter Temperatur zu acy- lieren.
Das auf diese Weise erhaltene N-[2-(3'- Methoxy-phenoxy)- äthyl-1] -N-methyl-pyrro- lidinoacetamid bildet ein farbloses, unter 0,06 mm bei 163-164 siedendes Öl.
Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung wei terer Derivate Verwendung finden. <I>Beispiel:</I> 17g N-[2-(3'-Methoxy-phenoxy)-äthyl-1]- amin in Benzol werden mit einer Mischung von 19 g Pyrrolidinoessigsäure-chlorid-hydro- chlorid und 20 g Triäthylamin erwärmt.
An- schliessend wird das gebildete Triäthylamin- hydrochlorid durch Ausschütteln mit Wasser entfernt., die Benzollösung nach dem Trock nen verdampft und der Rückstand im Hoch vakuum destilliert. Man erhält so in guter Ausbeute das N- [2- (3'-Methoxy-phenoxy)- äthyl-1]-N-methyl-pyrrolidinoacetamid, wel ches ein unter 0,06 mm bei 163-164 sieden des farbloses Öl darstellt.
Die Reaktion kann auch ohne Verdiin- nungs- und Kondensationsmittel durchgeführt werden, indem man beispielsweise das N-[2- (3'-lvlethoxy-phenoxy)-äthyl-1]-amin mit Pyr- rolidinoessigsäure-ehlorid-hydrochlorid trok- ken erhitzt, anschliessend die Reaktionsmas;@e 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 production of a new basic substituted fatty acid amide, which is characterized in that a compound of the formula is used
EMI0001.0009
a compound of the formula
EMI0001.0010
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, for example, the hydrochloride or (read sulfate.
Examples of possible compounds of formula II are: pyrrolidinoacetic acid itself and its reactive functional derivatives such as its halides, its esters, its anhydrides, for example the pure and also the mixed anhydrides with phosphoric acid, sulfuric acid and carbonic acid, etc.
For example, N- [2- (3'-methoxyphenoxp) ethyl-1] amine or a salt thereof can be treated with pyrrolidinoacetic acid in the presence of a dehydrating agent suitable for this purpose, such as phosphorus pentoxide, phosphorus oxychloride, etc. Furthermore, N- [2- (3'-methoxyphenoxy) ethyl-1] amine or a salt thereof can also be reacted with a pyrrolidinoacetic acid halide (or a salt of such) or an anhydride.
It is furthermore also possible to acylate N- [2- (3'-methoxyphenoxy) ethyl-1] amine with a pyrrolidinoacetic acid ester, preferably an aryl ester, at an elevated temperature.
The N- [2- (3'-methoxyphenoxy) -ethyl-1] -N-methyl-pyrrolidinoacetamide obtained in this way forms a colorless oil boiling below 0.06 mm at 163-164.
The new amide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. <I> Example: </I> 17 g of N- [2- (3'-methoxy-phenoxy) -ethyl-1] -amine in benzene are mixed with a mixture of 19 g of pyrrolidinoacetic acid chloride hydrochloride and 20 g of triethylamine warmed.
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- (3'-methoxyphenoxy) - ethyl-1] -N-methyl-pyrrolidinoacetamide, which represents a colorless oil boiling below 0.06 mm at 163-164, is thus obtained in good yield.
The reaction can also be carried out without diluting and condensing agents, for example by heating the N- [2- (3'-lethoxy-phenoxy) -ethyl-1] -amine to dryness with pyrrolidinoacetic acid chloride hydrochloride , then the reaction mixture diluted with water and worked up in the usual way.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311577T | 1952-06-08 | ||
| CH306201T | 1955-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311577A true CH311577A (en) | 1955-11-30 |
Family
ID=25735104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311577D CH311577A (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) | CH311577A (en) |
-
1952
- 1952-06-08 CH CH311577D patent/CH311577A/en unknown
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