CH311689A - 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
- CH311689A CH311689A CH311689DA CH311689A CH 311689 A CH311689 A CH 311689A CH 311689D A CH311689D A CH 311689DA CH 311689 A CH311689 A CH 311689A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- amide
- fatty acid
- substituted fatty
- new basic
- 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 3
- 239000000194 fatty acid Substances 0.000 title claims description 3
- 229930195729 fatty acid Natural products 0.000 title claims description 3
- 150000004665 fatty acids Chemical class 0.000 title claims description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 238000009835 boiling Methods 0.000 claims description 3
- 239000012230 colorless oil Substances 0.000 claims description 3
- IPXNXMNCBXHYLQ-UHFFFAOYSA-N 2-pyrrolidin-1-ylacetic acid Chemical compound OC(=O)CN1CCCC1 IPXNXMNCBXHYLQ-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 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 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 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
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 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
- Pyrrole Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides. Gegenstand des vorliegenden Patentes bil det ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäurea.mides, wel.- ehes dadurch gekennzeichnet. ist, dass man eine Verbindung der Formel,
EMI0001.0007
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Pyrrolidin umsetzt.
Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austausch gegen den basischen Rest. geeigneten reaktionsfähi gen Substituenten, wie z. B. einer Alkylsul- fonyioxy- oder Arylsulfonyloxygruppe, beste lien. Der Austausch der Gruppe X gegen den Pyrrolidinorest erfolgt z. B. durch einfaches Erwärmen mit. Pyrrolidin, gegebenenfalls in Gegenwart. eines basisch reagierenden Kon- densationsmittels oder von Pvrrolidin im Überschuss.
Das Pyrrolidinoessigsäure-N- (3 phenoxy-propyl-2)-amid ist. ein farbloses, un ter 0,07 mm bei 143-144 siedendes Öl.
Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung wei terer Derivate Verwendung finden.
Beispiel: 45,0g Chlor essigsäur e-2NT- (3-phenoxy-pro- py1--.)-amid und 30,0 g Pyrrolidin werden zu- sammen in 300 cms abs. Benzol 4 Stunden auf dem Wasserbad erhitzt.. Das Reaktionsgemisch wird mit Wasser ausgeschüttelt und dann mit 2n-Salzsäure ausgezogen.
Darauf wird der salzsaure Auszug mit Äther extrahiert, unter Eiskühlung mit konz. Natronlauge versetzt lind das ausgeschiedene Öl in Äther aufge nommen. Nach dem Trocknen der Ätheraus züge über Pottasche wird der Äther verdampft und der Rückstand im Hochvakuum destilliert.
Dabei gewinnt. man das unter 0,07 mm bei 143-144 siedende Pyrrolidinoessigsäure-N- (3-phenoxy-propyl-2)-a.mid in einer Ausbeute von 78 1/o- der Theorie. Farbloses Öl, schwer löslich in Wasser, gut in organischen Lösungs mitteln und in. verdünnten Mineralsäuren.
Process for the production of a new basic substituted fatty acid amide. The subject of the present patent bil det a process for the production of a new basic substituted Fettsäurea.mides, wel.- ehes characterized. is that you can find a compound of the formula
EMI0001.0007
in which X is a reactive radical which is split off during the reaction, reacts with pyrrolidine.
The radical X can be in a halogen atom or another for the exchange against the basic radical. Suitable reactive substituents such. B. an alkylsulfonyioxy or arylsulfonyloxy group, best lien. The exchange of group X against the pyrrolidino radical takes place, for. B. by simply heating with. Pyrrolidine, optionally in the presence. a basic condensing agent or an excess of pvrrolidine.
The pyrrolidinoacetic acid N- (3-phenoxy-propyl-2) -amide is. a colorless oil boiling below 0.07 mm at 143-144.
The new amide is to be used as a local anesthetic and as an intermediate for the production of further derivatives.
Example: 45.0 g of chloroacetic acid e-2NT- (3-phenoxy-propy1 -.) - amide and 30.0 g of pyrrolidine are added together in 300 cms abs. Benzene heated on a water bath for 4 hours. The reaction mixture is extracted by shaking with water and then extracted with 2N hydrochloric acid.
The hydrochloric acid extract is then extracted with ether, with conc. Sodium hydroxide is added and the excreted oil is absorbed in ether. After the ether extracts have dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.
It wins. the pyrrolidinoacetic acid-N- (3-phenoxy-propyl-2) -a.mid boiling below 0.07 mm at 143-144 in a yield of 78 1 / o of theory. Colorless oil, sparingly soluble in water, good in organic solvents and in dilute mineral acids.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311689T | 1952-06-08 | ||
| CH307799T | 1952-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311689A true CH311689A (en) | 1955-11-30 |
Family
ID=25735422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311689D CH311689A (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) | CH311689A (en) |
-
1952
- 1952-06-08 CH CH311689D patent/CH311689A/en unknown
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