CH311623A - 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
- CH311623A CH311623A CH311623DA CH311623A CH 311623 A CH311623 A CH 311623A CH 311623D A CH311623D A CH 311623DA CH 311623 A CH311623 A CH 311623A
- Authority
- CH
- Switzerland
- Prior art keywords
- anilide
- methyl
- production
- fatty acid
- halogen
- Prior art date
Links
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 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 mann eine Verbindung der Formel
EMI0001.0009
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit.
Dimethylamin 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- fonyloxy- oder Arylsulfonyloxygruppe, beste hen. Der Austausch der Grippe X gegen den Dimethylaminrest erfolgt z.
B. durch einfaches Erwärmen mit Dimethylamin gegebenenfalls in Gegenwart eines basisch reagierenden Kon densationsmittels oder von Dimethylamin im L'berschuss. Das ss - Dimethylamino - propion- säure-(2-chlor-6-methyl-anilid) ist ein farbloses, auch im Hochvakuum nicht unzerset.zt sieden des Öl. Das Hydrochlorid der Base schmilzt bei 77,5-79,5 .
Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung wei terer Derivate Verwendung finden. <I>Beispiel:</I> 30 Gewichtsteile ss-Chlorpropionsäure-(2- chlor-6-methyl-anilid) (gewonnen durch Um setzen von 2-Chlor-6-methyl-anilin mit ss-Chlor- propionylchlorid in Gegenwart von Natrüun- acetat, Schmp. l09-112 )
werden in 180 Ge wichtsteilen Methanol suspendiert und mit<B>135</B> Gewichtsteilen wässriger 33o/oiger Dimethyl- aminlösung versetzt. Die Temperatur steigt dabei leicht an und ein grosser Teil des Re aktionsgemisches geht in Lösung. Nun wird während 1 Stunden bei Zimmertemperatur gerührt und dann einige Stunden bei 60-70 .
Eine Probe mit Wasser und nachfolgend mit verdünnter Salzsäure versetzt ergibt. wieder Lösung des ausgefallenen Niederschlages. Mit Wasserdampf wird hierauf der Alkohol und das überschüssige Dimethylamin abgeblasen und nach dem Erkalten und Sättigen der wässrigen Lösung mit Natriumchlorid das zu rückbleibende Öl in Äther aufgenommen. Nach dem Trocknen der ätherischen Lösung und Verjagen des Lösungsmittels verbleibt ein Öl, das durch Überführen in das Hydrochlorid gereinigt wird.
Man erhält 65 Gewichtsteile reines ss-Dimethylamino-propionsäure-(2-chlor- 6-methyl-anilid). Die Umsetzung mit Dime- thylamin kann auch in Benzol stattfinden.
Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). Subject of the present patent bil det. a process for the preparation of a new basic substituted fatty acid (2-halogen 6-methyl-anilide), which is characterized in that a compound of the formula
EMI0001.0009
in which X denotes a reactive radical which is split off during the reaction, with.
Dimethylamine converts.
The radical X can be in a halogen atom or another for the exchange against the basic radical. Suitable reactive substituents such. B. an alkylsulfonyloxy or arylsulfonyloxy group, best hen. The exchange of flu X against the dimethylamine residue takes place z.
B. by simply heating with dimethylamine, optionally in the presence of a basic reacting Kon densantsmittel or of dimethylamine in excess. The ss - dimethylamino - propionic acid (2-chloro-6-methyl-anilide) is a colorless oil that does not boil undecomposed even in a high vacuum. The base hydrochloride melts at 77.5-79.5.
The new anilide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. <I> Example: </I> 30 parts by weight of ß-chloropropionic acid (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with ß-chloropropionyl chloride in the presence of Sodium acetate, m.p. 109-112)
are suspended in 180 parts by weight of methanol and <B> 135 </B> parts by weight of aqueous 33% dimethylamine solution are added. The temperature rises slightly and a large part of the reaction mixture goes into solution. The mixture is then stirred for 1 hour at room temperature and then for a few hours at 60-70.
A sample with water and then mixed with dilute hydrochloric acid results. again dissolution of the precipitate. The alcohol and the excess dimethylamine are then blown off with steam and, after the aqueous solution has cooled and saturated with sodium chloride, the remaining oil is taken up in ether. After drying the essential solution and driving off the solvent, an oil remains which is purified by converting it into the hydrochloride.
65 parts by weight of pure β-dimethylamino-propionic acid (2-chloro-6-methyl-anilide) are obtained. The reaction with dimethylamine can also take place in benzene.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH311623T | 1952-02-25 | ||
CH307799T | 1952-11-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH311623A true CH311623A (en) | 1955-11-30 |
Family
ID=25735356
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH311623D CH311623A (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) | CH311623A (en) |
-
1952
- 1952-02-25 CH CH311623D patent/CH311623A/en unknown
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