CH311575A - 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
- CH311575A CH311575A CH311575DA CH311575A CH 311575 A CH311575 A CH 311575A CH 311575D A CH311575D A CH 311575DA CH 311575 A CH311575 A CH 311575A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- fatty acid
- production
- acid amide
- new basic
- Prior art date
Links
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 4
- IPXNXMNCBXHYLQ-UHFFFAOYSA-N 2-pyrrolidin-1-ylacetic acid Chemical compound OC(=O)CN1CCCC1 IPXNXMNCBXHYLQ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 150000008064 anhydrides Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- -1 pyrrolidinoacetic acid halide Chemical class 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
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000003085 diluting agent Substances 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
- 239000000203 mixture Substances 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil 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
- 238000002360 preparation method Methods 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
Description
<B>Verfahren zur Herstellung eines neuen basisch substituierten</B> 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
EMI0001.0003
eine Verbindung der Formel
EMI0001.0005
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 kom men beispielsweise in Frage: Pyrrolidino- essigsäure 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 Koh lensäure usf.
Man kann beispielsweise N-[2-(3'-Methyl- phenoxy )-äthyl-1]-N-methyl-amin oder auch ein Salz desselben in Gegenwart eines für diese Zwecke geeigneten wasserabspaltenden Mittels wie Phosphorpentoxyd, Phosphoroxy- ehlorid usf. mit. Pyrrolidinoessigsäure behan deln.
Weiter kann man auch N- [ 2- (3'-Methyl- phenoxy)-äthyl-1]-N-methyl-amin bzw. ein Salz desselben mit einem Pyrrolidinoessig- säurehalogenid (bzw. einem Salz eines sol chen) oder einem Anhy drid zur Reaktion bringen.
Es ist weiterhin auch möglich, NT-[2-(3'- Methyl-phenoxy)-äthyl-1]-N-methyl-amin mit einem Pyrrolidinoessigsäureester, vorzugs weise einem Arylester, bei erhöhter Tempera tur zu acylieren.
Das auf diese Weise erhaltene N-[2-(3'- Methyl -phenoxy) - äthyl-1 ] - N - methyl-pyr roli- dino-acetamid bildet ein farbloses, unter 0,06 mm bei 151-152 siedendes Öl.
Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung wei terer Derivate Verwendung finden.
<I>Beispiel:</I> 16 g hlT [2-(3'-i@lethyl-phenoxy)-äthyl-1]-N- methyl-amin in Benzol werden mit einer Mi schung von 7.9 g Pyrrolidinoessigsätire-chlo- rid-hydrochlorid und 20 g Triäthylamin er wärmt. Anschliessend wird das gebildete Tri- äthylaminhydroelilorid durch Ausschütteln mit Wasser entfernt, die Benzollösung nach dem Trocknen verdampft und der Rückstand im IIoclivakuum destilliert.
Man erhält so in guter Ausbeute das N-[2-(3'-Methyl-phenoxy)- äthyl-1]-N-methyl-pyrrolidino-acetamid, wel- ches ein unter 0,06 mm bei 151-152 sieden des farbloses Öl darstellt.
Die Reaktion kann auch ohne Verdün n inigs- und Kondensationsmittel durchge führt erden, indem man beispielsweise das NL [2- (3'-Methy 1-plienoxy) -äthyl-1 ] - N- methyl- amin mit Pvrrolidinoessigsäure-chlorid-hydro- ehlorid trocken erhitzt, anschliessend die Re aktionsmasse mit Wasser verdünnt und in üblicher Weise aufarbeitet.
<B> Process for the production of a new basic substituted </B> 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
EMI0001.0003
a compound of the formula
EMI0001.0005
in which formulas X and Y are reactive residues that are split off during the reaction.
As connections. of formula I are, for example, possible for a conversion: The free amine (Y = H), but also its salts, such as the hydrochloride or the sulfate.
Examples of 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 carbon acid, etc.
For example, N- [2- (3'-methylphenoxy) ethyl-1] -N-methylamine or a salt thereof in the presence of a dehydrating agent suitable for this purpose, such as phosphorus pentoxide, phosphorus oxychloride, etc., can be used . Treat pyrrolidinoacetic acid.
Furthermore, N- [2- (3'-methylphenoxy) ethyl-1] -N-methyl-amine or a salt thereof with a pyrrolidinoacetic acid halide (or a salt of such) or an anhy get drid to react.
It is also possible to acylate NT- [2- (3'-methyl-phenoxy) -ethyl-1] -N-methyl-amine with a pyrrolidinoacetic acid ester, preferably an aryl ester, at an elevated temperature.
The N- [2- (3'-methylphenoxy) - ethyl-1] - N - methyl-pyrrolidino-acetamide obtained in this way forms a colorless oil which boils below 0.06 mm at 151-152.
The new amide is to be used as a local anesthetic and as an intermediate for the production of further derivatives.
<I> Example: </I> 16 g of hlT [2- (3'-i @ lethyl-phenoxy) -ethyl-1] -N-methyl-amine in benzene are chlorinated with a mixture of 7.9 g of pyrrolidinoacetic acid rid hydrochloride and 20 g of triethylamine it warms. The triethylamine hydroeliloride formed is then removed by shaking with water, the benzene solution is evaporated after drying and the residue is distilled in a vacuum.
The N- [2- (3'-methyl-phenoxy) -ethyl-1] -N-methyl-pyrrolidino-acetamide, which boils below 0.06 mm at 151-152 of the colorless one, is obtained in good yield Represents oil.
The reaction can also be carried out without a diluent and condensing agent by, for example, the NL [2- (3'-Methy 1-plienoxy) ethyl-1] - N-methyl amine with pvrrolidinoacetic 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 |
|---|---|---|---|
| CH311575T | 1952-06-08 | ||
| CH306201T | 1955-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311575A true CH311575A (en) | 1955-11-30 |
Family
ID=25735102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311575D CH311575A (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) | CH311575A (en) |
-
1952
- 1952-06-08 CH CH311575D patent/CH311575A/en unknown
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