CH311576A - 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
- CH311576A CH311576A CH311576DA CH311576A CH 311576 A CH311576 A CH 311576A CH 311576D A CH311576D A CH 311576DA CH 311576 A CH311576 A CH 311576A
- Authority
- CH
- Switzerland
- Prior art keywords
- fatty acid
- substituted fatty
- production
- ethyl
- acid amide
- 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 description 2
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 3
- -1 diethylaminoacetic acid halide Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 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 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- BITBVQPNBZYTBL-UHFFFAOYSA-N 2-(diethylamino)acetyl chloride;hydrochloride Chemical compound Cl.CCN(CC)CC(Cl)=O BITBVQPNBZYTBL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-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
- 150000001412 amines Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 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
- 239000002253 acid Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 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
- 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
- 150000004820 halides Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000003589 local anesthetic agent 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
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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 neuen basisch substituierten Fettsäureamides.
Gegenstand des vorliegenden Patentes ist cin Verfahren zur Herstellung eines neuen basisel substituierten Fettsaureamides, wel ehes dadurch gekennzeiehnet ist, dass man auf eine Verbindung der Formel
EMI1.1
eine Verbindung der Formel
EMI1.2
in welchen Formeln X und y reaktionsfähige, hei der Reaktion sich abspaltende Reste bedeuten, einwirken lässt.
Als Verbindungen der Formel I kommen für einen Umsatz beispielsweise in Frage : Das freie Amin (Y = H), aber aueh dessen salé, wie beispielsweise das Hydroeblorid oder das Sulfat.
Als Verwindungen der Formel II kommen beispielsweise in Frage : Diäthylaminoessig- saure selbst und ihre reaktionsfähigen funktionellen Derivate wie ihre Halogenide, ihre Ester, ihre Anhydride, beispielsweise die reinen und nach die gemischten Anhydride mit Phosphorsäure, Schwefelsäure und Kohlensäure usf.
MAn kann beispielsweise N-[o-(3'-Methoxy- phenoxy)-äthyl-1]-N-methylamin oder auch ein Salz desselben in Gegenwart eines fur diese Zweeke geeigneten wasserabspaltenden 3Iittels wie Phosphorpentoxyd, Phosphoroxy- chlorid use, mit Diäthylaminoessigsäure behandeln.
Weiter kann man auch N- [2- (3'-Methoxyphenoxy)-äthyl-1]-N-methyl;amin bzw. ein Salz desselben mit einem Diäthylaminoessigsäure- halogenid (bzw. einem Salz eines solchen) oder einem Anhydrid zur Reaktion bringen.
Es ist weiterhin auch moglich, N- [2- (3 = MEthoxy-phenoxy)-äthyl-1]-N-methylamin mit einem : Didthylaminoessigsaureester, vorzugsweise einem Arylester, bei erhöhter Tempera tur zu acylieren.
Das au dise Weise erhaltene N-[2-(3'- Methoxy-phenoxy)-äthyl-1]-N-methyl-diäthyl- amino-acetamid bildet ein farbloses, unter 0, 06 mm bei 157-158 siedendes 61.
Das neue Amid soll als Lokalanästhetikum und als Zwisechenprodukt zur Eerstellung wei- terer Derivate Verwendlmg finden.
Beispiel :
17 g N-[2-(3'-Methoxy-phenoxy)-äthyl-1] N-methylamin in Benzol werden mit einer Mischung von 18 g Diäthylaminoessigsäure- ehlorid-hydrochlorid lmd 20 g Triäthylamin erwärm. Anschliessend wird das geXildete Triäthylaminhydrochlorid durch Ausschütteln mit Wasser entfernt, die Benzoll6sung nach dem Trocknen verdampft und der Rüek- stand im hochvakuum destilliert. Man erhält so in guter Ausbeute das N- [2- (3'-Methoxyphenoxy)-äthyl-1]-N-methyl-diäthylamino acetamid, welehes ein unter 0, 06 mm bei 157 bis 158 siedendes farbloses 01 darstellt.
Die CReaktion kann aueh ohne Verdün- nungs-und Kondensationsmittel durchgeführt werden, indem man beispielsweise dasn N-[2 (3'-Methoxy-Phenoxy)-äthyl-1]-N-methylamin mit Diäthylaminoessigsäure-chlorid-hydrochlorid troeken erhitzt, anschliel3end die Reak- tionsmasse mit Wasser verdünnt und in oubli- cher Weise auíarbeitet.
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 base-substituted fatty acid amide, which is marked by the fact that a compound of the formula
EMI1.1
a compound of the formula
EMI1.2
in which formulas X and y mean reactive radicals which are split off during the reaction, can act.
Compounds of the formula I that can be used for a conversion are, for example: The free amine (Y = H), but also its salé, such as, for example, the hydrochloride or the sulfate.
Twists of the formula II include, for example: diethylaminoacetic acid itself and its reactive functional derivatives such as its halides, its esters, its anhydrides, for example the pure and mixed anhydrides with phosphoric acid, sulfuric acid and carbonic acid etc.
For example, N- [o- (3'-methoxyphenoxy) ethyl-1] -N-methylamine or a salt thereof can be treated with diethylaminoacetic acid in the presence of a dehydrating agent suitable for these purposes, such as phosphorus pentoxide or phosphorus oxychloride .
N- [2- (3'-methoxyphenoxy) ethyl-1] -N-methyl; amine or a salt thereof can also be reacted with a diethylaminoacetic acid halide (or a salt of such) or an anhydride .
It is also possible to acylate N- [2- (3 = methoxy-phenoxy) -ethyl-1] -N-methylamine with a didthylaminoacetic acid ester, preferably an aryl ester, at elevated temperature.
The N- [2- (3'-methoxyphenoxy) -ethyl-1] -N-methyl-diethylamino-acetamide obtained in this way forms a colorless 61 boiling below 0.06 mm at 157-158.
The new amide is to be used as a local anesthetic and as an intermediate product for the preparation of further derivatives.
Example:
17 g of N- [2- (3'-methoxyphenoxy) ethyl-1] N-methylamine in benzene are heated with a mixture of 18 g of diethylaminoacetic acid chloride hydrochloride and 20 g of triethylamine. 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-diethylamino acetamide, which is a colorless oil boiling below 0.06 mm at 157 to 158, is thus obtained in good yield.
The C reaction can also be carried out without a diluent and condensing agent, for example by heating the N- [2 (3'-methoxy-phenoxy) -ethyl-1] -N-methylamine to dryness with diethylaminoacetic acid chloride hydrochloride, then heating the Reaction mass diluted with water and worked up in an obvious way.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH311576T | 1952-06-08 | ||
CH306201T | 1955-03-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH311576A true CH311576A (en) | 1955-11-30 |
Family
ID=25735103
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH311576D CH311576A (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) | CH311576A (en) |
-
1952
- 1952-06-08 CH CH311576D patent/CH311576A/en unknown
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