CH311700A - 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
- CH311700A CH311700A CH311700DA CH311700A CH 311700 A CH311700 A CH 311700A CH 311700D A CH311700D A CH 311700DA CH 311700 A CH311700 A CH 311700A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- fatty acid
- acid amide
- production
- substituted fatty
- 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 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 20
- 238000009835 boiling Methods 0.000 claims description 3
- 229940080818 propionamide Drugs 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AUHYZQCEIVEMFH-UHFFFAOYSA-N 2-bromopropanamide Chemical group CC(Br)C(N)=O AUHYZQCEIVEMFH-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides. Gegenstand des vorliegenden Patentes bil det ein Verfahren zur Herstellung eines neuen basiseh substituierten Fettsäureamides, wel ches dadurch gekennzeichnet ist, dass man eine Verbindung der Formel
EMI0001.0005
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Pyrrolidin umsetzt. Der Rest.
X kann in einem Halogenatom (;der einem sonstigen für den Austausch gegen den basischen Rest geeigneten reaktionsfähi gen Substituenten, wie zum Beispiel einer Al- )tyIsulfonyloxy- oder Arylsulfonyloxygruppe, bestehen.
Der Austausch der Gruppe X gegen den Pyrrolidinrest erfolgt zum Beispiel durch einfaches Erwärmen mit Pyrrolidin, gegebe nenfalls in Gegenwart eines basisch reagieren den Kondensationsmittels, oder von Pyrrolidin im Überschuss. Das N-(2-Phenoxy-äthyl-1)-N- methyl-a-py-rrolidino-propionamid ist ein farb loses, unter 0,05 mm bei 140-141 sieden des Öl.
Das neue Amid soll als Lokalanästhetikum lind als Zwischenprodukt zur Herstellung wei terer Derivate Verwendung finden. <I>Beispiel:</I> 28,6 g N-(2-Phenoxy-äthyl-1)-N-methyl-u= brom-propionamid und 13,4 g Pyrrolidin wer den zusammen in 150 ems abs. Benzol 6 Stun den auf dem Wasserbad erhitzt. Das Reak tionsgemisch wird mit Wasser ausgeschüttelt und dann mit 2n-Salzsäure ausgezogen.
Dar auf wird der salzsaure Auszug mit Äther extrahiert, unter Eiskühlung mit konz. Na tronlauge versetzt und das ausgeschiedene Öl in Äther aufgenommen. Nach dem Trocknen der Ätherauszüge über Pottasche wird der Äther verdampft und der Rückstand im Hochvakuum destilliert.
Dabei gewinnt man das unter 0,05 mm bei 340-141 siedende N-(2-Phenoxy-äthyl-3.)-N- methy-l-a-p@#rrolidino-propionamid als farb loses, säurelösliches Öl.
Process for the production of a new basic substituted fatty acid amide. The subject of the present patent forms a process for the preparation of a new basic substituted fatty acid amide, which is characterized in that a compound of the formula
EMI0001.0005
in which X is a reactive radical which is split off during the reaction, reacts with pyrrolidine. The rest.
X can be in a halogen atom (another reactive substituent suitable for replacement with the basic radical, such as an al-) tyIsulfonyloxy- or arylsulfonyloxy group.
The group X is exchanged for the pyrrolidine radical, for example, by simply heating with pyrrolidine, possibly in the presence of a basic reacting condensation agent, or of pyrrolidine in excess. The N- (2-phenoxy-ethyl-1) -N-methyl-a-py-rrolidino-propionamide is a colorless, below 0.05 mm at 140-141 boiling of the oil.
The new amide is to be used as a local anesthetic and as an intermediate for the production of other derivatives. <I> Example: </I> 28.6 g of N- (2-phenoxy-ethyl-1) -N-methyl-u = bromopropionamide and 13.4 g of pyrrolidine are put together in 150 ems abs. Benzene heated on a water bath for 6 hours. The reaction mixture is extracted with water and then extracted with 2N hydrochloric acid.
Then the hydrochloric acid extract is extracted with ether, with ice cooling with conc. Sodium hydroxide solution was added and the oil which had separated out was taken up in ether. After the ether extracts have been dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.
The N- (2-phenoxy-ethyl-3.) - N-methy-l-a-p @ # rrolidino-propionamide, boiling below 0.05 mm at 340-141, is obtained as a colorless, acid-soluble oil.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311700T | 1952-06-08 | ||
| CH307799T | 1952-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311700A true CH311700A (en) | 1955-11-30 |
Family
ID=25735433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311700D CH311700A (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) | CH311700A (en) |
-
1952
- 1952-06-08 CH CH311700D patent/CH311700A/en unknown
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