CH311617A - 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
- CH311617A CH311617A CH311617DA CH311617A CH 311617 A CH311617 A CH 311617A CH 311617D A CH311617D A CH 311617DA CH 311617 A CH311617 A CH 311617A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- anilide
- halogen
- fatty acid
- substituted fatty
- Prior art date
Links
Classifications
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- 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
- C07D295/145—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 with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—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 with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- 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
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- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (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 Fettsälure-(2-hal.ogen-6- methyl-a.nilids), welches dadurch gekennzeich net ist, dass man eine Verbindung der Formel
EMI0001.0009
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest, bedeutet, mit 2-Methyl-piperidin umsetzt.
Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austausch gegen den basischen Rest geeigneten reaktionsfähi ren Substituenten, wie z. B. einer Alky1sul- fonyloxy- oder Arylsulfonyloxygruppe, beste hen.
Der Austausch der Gruppe X gegen den 2-Methyl-piperidinrest erfolgt. z."B. durch ein faches Erwärmen mit 2-Methyl-piperidin ge gebenenfalls in Gegenwart eines basisch re agierenden Kondensationsmittels oder von 2- Methyl-piperidin im -Überschuss. Das N-2-Me- thy 1-piperidino-a.cet-(2'-ehlor-6'-methyl-anilid) ist ein Öl, das nach einiger Zeit zu farblosen, bei 97-98 schmelzenden Kristallen erstarrt. Das Hydrochlorid der Base schmilzt bei<B>177</B> bis l80 .
Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung wei terer Derivate Verwendung finden. <I>Beispiel:</I> 36 Gewichtsteile Chloracet-(2-chlor-6-me- thyl-anilid) (gewonnen durch Umsetzen von 2- Chlor-6-methyl-anilin mit Chloracetylchlorid in Gegenwart von Natriumaeetat, Schmp. 140 bis 141 ) werden in 7 0 Gewichtsteilen Äthanol suspendiert und mit 42 Gewichtsteilen 2-Me- thyl-piperidin versetzt.
Die Temperatur steigt dabei leicht an und ein grosser Teil des Reak tionsgemisches geht in Lösung. Nun wird wäh rend 4 Stunden bei Zimmertemperatur ge rührt und dann einige Stunden bei 65-75 . 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 2-1Vlethyl-piperidin abgebla sen und nach dem Erkalten das zurückblei bende Öl in Äther aufgenommen. Nach dem Trocknen der ätherischen Lösung und Ver jagen des Lösungsmittels verbleibt ein Öl, das durch Vakuumdestillation gereinigt wird.
Man erhält 40 Gewichtsteile reines N-2-Methyl- piperidino-acet-(2'-chlor-6'-methyl-anilid), was einer Ausbeute von 87 % entspricht. Die Um- setzung mit 2-Methyl-piperidin kann auch in Benzol stattfinden.
Process for the production of a new basic substituted fatty acid (2-halogen-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-a.nilids), which is characterized in that a compound of the formula
EMI0001.0009
in which X is a reactive radical which is split off during the reaction, is reacted with 2-methylpiperidine.
The radical X can be in a halogen atom or other suitable reactive substituents for replacement with the basic radical, such as. B. an alky1sulfonyloxy or arylsulfonyloxy group, best hen.
The group X is exchanged for the 2-methylpiperidine residue. z. "E.g. by single heating with 2-methyl-piperidine, optionally in the presence of a basic-reacting condensing agent or of 2-methyl-piperidine in excess. The N-2-methy 1-piperidino-a.cet - (2'-chloro-6'-methyl-anilide) is an oil that solidifies after some time to colorless crystals that melt at 97-98. The hydrochloride of the base melts at <B> 177 </B> to 180.
The new anilide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. <I> Example: </I> 36 parts by weight of chloroacet- (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with chloroacetyl chloride in the presence of sodium acetate, melting point 140 to 141) are suspended in 70 parts by weight of ethanol and mixed with 42 parts by weight of 2-methylpiperidine.
The temperature rises slightly and a large part of the reaction mixture goes into solution. The mixture is then stirred for 4 hours at room temperature and then for a few hours at 65-75. A sample with water and then mixed with dilute hydrochloric acid results in a solution of the precipitate. The alcohol and the excess 2-1Vlethyl-piperidine are then blown off with steam and, after cooling, the remaining oil is taken up in ether. After the essential solution has dried and the solvent has been chased away, an oil remains which is purified by vacuum distillation.
40 parts by weight of pure N-2-methylpiperidino-acet- (2'-chloro-6'-methyl-anilide) are obtained, which corresponds to a yield of 87%. The reaction with 2-methylpiperidine can also take place in benzene.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH311617T | 1952-02-25 | ||
CH307799T | 1952-11-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH311617A true CH311617A (en) | 1955-11-30 |
Family
ID=25735350
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH311617D CH311617A (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) | CH311617A (en) |
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1952
- 1952-02-25 CH CH311617D patent/CH311617A/en unknown
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