CH311657A - 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
- CH311657A CH311657A CH311657DA CH311657A CH 311657 A CH311657 A CH 311657A CH 311657D A CH311657D A CH 311657DA CH 311657 A CH311657 A CH 311657A
- Authority
- CH
- Switzerland
- Prior art keywords
- diethylamine
- ethylamide
- propyl
- radical
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 7
- 239000000194 fatty acid Substances 0.000 title claims description 7
- 229930195729 fatty acid Natural products 0.000 title claims description 7
- 150000004665 fatty acids Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000284 extract Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000003589 local anesthetic agent Substances 0.000 claims description 3
- MDUQQNWSTJAPCW-UHFFFAOYSA-N (ethyl-$l^{2}-azanyl)ethane Chemical compound CC[N]CC MDUQQNWSTJAPCW-UHFFFAOYSA-N 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 235000010755 mineral Nutrition 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229940072033 potash Drugs 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000012230 colorless oil Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- 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 FettsÏureamides.
Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basiseh substituierten Fettsäureamides, welches dadurch gekennzeichnet ist, dass man eine Verbindung der Formel
EMI1.1
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Diäthylamin umsetzt.
Der Rest X kann in einem Halogenatom oder einem sonstigen f r den Austauseh gegen den basischen Rest geeigneten reaktionsfähigen Substituenten, wie zum Beispiel Alkyl- sulfonyloxy-oder Arylsulfonyloxygruppe, bestehen. Der Austausch der Gruppe X gegen den Diäthylaminorest erfolgt zum Beispiel durch einfaches Erwärmen mit Diäthylamin, gegebenenfalls in Gegenwart eines basisch reagierenden Kondensationsmittels oder von Diäthylamin im Überschuss. Das Diäthyl- aminoessigsäure-N- [3- (2', 4'-dimethyl-phen- oxy)-propyl-2]-äthylamid ist ein farbloses, unter 0, 02 mm bei 151 siedendes 61.
Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden.
Beispiel :
28, 3 g Chloressigsäure-N- [3- (2', 4'-dimethyl phenoxy)-propyl-2]-äthylamid und 15, 0 g Di äthylamin werden zusammen in 200 cm3 abs.
Benzol l Stunde auf dem Wasserbad erhitzt.
Das Reaktionsgemisch wird mit Wasser ausgeschüttelt und dann mit 2n-Salzsäure ausgezogen. Darauf wird der salzsaure Auszug mit Xther extrahiert, unter Eiskühlung mit konz. Natronlauge versetzt und das ausgeschiedene öl in Äther aufgenommen. Nach dem Trocknen der Xtherauszüge über Pottasche wird der Äther verdampft und der Rückstand im Hochvakuum destilliert.
Dabei gewinnt man das unter 0, 02 mm bei 151 siedende Diäthylaminoessigsäure-N- [3- (2', 4'-dimethyl-phenoxy)-propyl-2]-Ïthylamid in einer Ausbeute von 71"/o der Theorie. Farb- loses 61, schwer löslich in Wasser, gut in or ganischen Lösungsmitteln und in verdünnten MineralsÏuren.
PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.2
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Diäthylamin umsetzt. Das auf diese Weise erhaltene Diäthylaminoessigsäure-N- [3- (2', 4'
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
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, which is characterized in that a compound of the formula
EMI1.1
in which X is a reactive radical which is split off during the reaction, is reacted with diethylamine.
The radical X can consist of a halogen atom or some other reactive substituent suitable for exchange with the basic radical, such as, for example, an alkylsulfonyloxy or arylsulfonyloxy group. Group X is exchanged for the diethylamino radical, for example, by simply heating with diethylamine, optionally in the presence of a basic condensing agent or excess diethylamine. Diethylaminoacetic acid-N- [3- (2 ', 4'-dimethyl-phenoxy) -propyl-2] -ethylamide is a colorless 61 boiling below 0.02 mm at 151.
The new amide will be used as a local anesthetic and as an intermediate for the production of other derivatives.
Example:
28, 3 g of chloroacetic acid-N- [3- (2 ', 4'-dimethyl phenoxy) propyl-2] ethylamide and 15, 0 g of diethylamine are combined in 200 cm3 of abs.
Benzene heated on a water bath for 1 hour.
The reaction mixture is extracted with water and then extracted with 2N hydrochloric acid. The hydrochloric acid extract is then extracted with Xther, with ice cooling with conc. Sodium hydroxide solution was added and the oil which had separated out was taken up in ether. After the extracts have been dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.
The diethylaminoacetic acid N- [3- (2 ', 4'-dimethylphenoxy) propyl-2] ethylamide, boiling below 0.02 mm at 151, is obtained in a yield of 71% of theory. loose 61, sparingly soluble in water, good in organic solvents and in dilute mineral acids.
PATENT CLAIM:
Process for the preparation of a new basic substituted fatty acid amide, characterized in that a compound of the formula
EMI1.2
in which X is a reactive radical which is split off during the reaction, is reacted with diethylamine. The diethylaminoacetic acid N- [3- (2 ', 4'
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311657T | 1952-06-08 | ||
| CH307799T | 1952-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311657A true CH311657A (en) | 1955-11-30 |
Family
ID=25735390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311657D CH311657A (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) | CH311657A (en) |
-
1952
- 1952-06-08 CH CH311657D patent/CH311657A/en unknown
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