CH311643A - Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). - Google Patents
Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).Info
- Publication number
- CH311643A CH311643A CH311643DA CH311643A CH 311643 A CH311643 A CH 311643A CH 311643D A CH311643D A CH 311643DA CH 311643 A CH311643 A CH 311643A
- Authority
- CH
- Switzerland
- Prior art keywords
- anilide
- methyl
- production
- fatty acid
- halogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 4
- 229930195729 fatty acid Natural products 0.000 title claims description 4
- 239000000194 fatty acid Substances 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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 150000003931 anilides Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- OXHOPZLBSSTTBU-UHFFFAOYSA-N 1,3-bis(bromomethyl)benzene Chemical compound BrCC1=CC=CC(CBr)=C1 OXHOPZLBSSTTBU-UHFFFAOYSA-N 0.000 description 1
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure. (2-halogen-6-methyl-anilids). Gegenstand des vorliegenden Patentes bil det ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6- methyl-anilids), welches dadurch gekennzeich net ist, dass man eine Verbindung der Formel
EMI0001.0004
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeu- det, mit Py rrolidin umsetzt.
Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austausch gegen den basischen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer Alkylsulfonyl- oxy- oder Arylsulfonyloxygruppe bestehen. Der Austausch der Gruppe X gegen den Pyr- rolidinrest erfolgt z. B. durch einfaches Er- wär-men mit Pyrrolidin gegebenenfalls in Ge genwart eines basisch reagierenden Konden sationsmittels oder von Pyrrolidin im Über schuss.
Das a-N-Pyrrolidino-capronsäure-(2- ehlor-6-methyl-anilid) ist ein säurelösliches Öl, das nach einiger Zeit zu farblosen, bei 55 schmelzenden Kristallen erstarrt. Das Hydro- chlorid der Base schmilzt\ bei 198-200 .
Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung wei terer Derivate Verwendung finden. <I>Beispiel:</I> 33 Gewichtsteile a-Brom -capronsäure- (2- chlor-6-methyl-anilid) (gewonnen durch Um setzen von 2-Chlor-6-methyl-anilin mit a-Brom- capronsäurebromid in Gegenwart von Na triumacetat, Schmp. 132 ) werden in 100 Ge wichtsteilen Äthanol suspendiert und mit 25 Gewichtsteilen Pyrrolidin versetzt.
Die, Temperatur steigt dabei leicht an, und ein grosser Teil des Reaktionsgemisches geht in Lö sung. Nun wird während 4 Stunden bei Zim mertemperatur gerührt und dann einige Stun den bei 65-70 . Das Ganze wird auf Wasser , gegossen, die wässrige Lösung mit Kochsalz ge sättigt und dann mit Äther extrahiert. Nach dem Trocknen der ätherischen Lösung und Verjagen des Lösungsmittels verbleibt ein Öl, das durch Überführen in das Hydrochlorid gereinigt wird. Man erhält 32 Gewichtsteile reines a-N-Pyrrolidino-capronsäure-(2-chlor-6- methyl-anilid). Die Umsetzung mit Pyrrolidin kann auch in Benzol stattfinden.
Process for the production of a new basic substituted fatty acid. (2-halo-6-methyl-anilide). The subject of the present patent bil det a process for the preparation of a new basic substituted fatty acid (2-halo-6-methyl-anilide), which is characterized in that a compound of the formula
EMI0001.0004
in which X signifies a reactive radical which is split off during the reaction, reacts with pyrrolidine.
The radical X can be in a halogen atom or any other reactive substituent suitable for replacement with the basic radical, such as. B. an alkylsulfonyl oxy or arylsulfonyloxy group. The exchange of group X against the pyrrolidine radical takes place z. B. by simply heating with pyrrolidine, possibly in the presence of a basic condensing agent or an excess of pyrrolidine.
The a-N-pyrrolidino-caproic acid- (2-chloro-6-methyl-anilide) is an acid-soluble oil that solidifies after some time to colorless crystals that melt at 55. The hydrochloride of the base melts at 198-200.
The new anilide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. <I> Example: </I> 33 parts by weight of a-bromo-caproic acid- (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with a-bromocaproic acid bromide in Presence of sodium acetate, melting point 132) are suspended in 100 parts by weight of ethanol and treated with 25 parts by weight of pyrrolidine.
The temperature rises slightly, and a large part of the reaction mixture goes into solution. The mixture is then stirred at room temperature for 4 hours and then for a few hours at 65-70. The whole thing is poured onto water, the aqueous solution is saturated with common salt and then extracted with ether. After drying the essential solution and driving off the solvent, an oil remains which is purified by converting it into the hydrochloride. 32 parts by weight of pure α-N-pyrrolidino-caproic acid (2-chloro-6-methyl-anilide) are obtained. The reaction with pyrrolidine can also take place in benzene.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311643T | 1952-02-25 | ||
| CH307799T | 1952-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311643A true CH311643A (en) | 1955-11-30 |
Family
ID=25735376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311643D CH311643A (en) | 1952-02-25 | 1952-02-25 | Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH311643A (en) |
-
1952
- 1952-02-25 CH CH311643D patent/CH311643A/en unknown
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