CH311581A - Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide). - Google Patents
Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide).Info
- Publication number
- CH311581A CH311581A CH311581DA CH311581A CH 311581 A CH311581 A CH 311581A CH 311581D A CH311581D A CH 311581DA CH 311581 A CH311581 A CH 311581A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- anilide
- halogen
- fatty acid
- substituted fatty
- Prior art date
Links
- 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
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000013078 crystal Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WXZHYWPLDRZBLZ-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)prop-2-enamide Chemical compound CC1=CC=CC(Cl)=C1NC(=O)C=C WXZHYWPLDRZBLZ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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
- 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
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung eines 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- met.hyl-anilids), welches dadurch gekennzeich net, ist, dass man eine Verbindung der Formel
EMI0001.0006
mit. --hIethyl-piperidin umsetzt. Die Umset zung kann in An- oder Abwesenheit von Lö- sungs- bzw. Verdünnungsmitteln und Anlage- f-imgska.talysatoren erfolgen.
Vorzugsweise wird wegen der Leiehtflüchtigkeit des 2-Me- thy1-piperidins unter Druek gearbeitet. Als Anlagerungskatalysatoren benützt man vor teilhaft quaternäre Ammoniumbasen, wie z. B. Trimethylbenzylammoniumhydroxyd.
Das so erhaltene ss-(2'-Methyl-piperidino)- propionsäure-(2-chlor-6-met.hyl-anilid) bildet ein farbloses Kristallpulver; dessen Hydro chlorid schmilzt bei 191-193 . Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden.
Beispiel: Ein Gemisch von 20 Gewichtsteilen Acryl säure-(2-chlor-6-methyl-anilid), 18 Gewichts- teilen 2-Methy 1-piperidin und einigen Tropfen Trimethylbenzyla.mmoniumhydroxyd wird im Autoklaven während 20 Stunden auf 145 erhitzt. Nach dem Erkalten wird durch die Reaktionsmischung Wasserdampf zwecks Ent fernung flüchtiger Anteile geleitet. Anschlie ssend wird verdampft und der Rückstand aus Pet.roläther umkristallisiert..
Man erhält so das ss- (2'-Methyl-piperidino) -propionsäure-2-chlor- 6-methyl-anilid als farbloses Kristallpulver.
Process for the production of a 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-met.hyl-anilids), which is characterized in that one is a compound of the formula
EMI0001.0006
With. - methyl piperidine converts. The implementation can take place in the presence or absence of solvents or diluents and system f-imgska.talysatoren.
Because of the volatility of 2-methy1-piperidine, it is preferable to work under pressure. As addition catalysts are used before some quaternary ammonium bases, such as. B. Trimethylbenzylammonium hydroxide.
The ss- (2'-methyl-piperidino) -propionic acid- (2-chloro-6-methyl-anilide) obtained in this way forms a colorless crystal powder; its hydrochloride melts at 191-193. The new anilide is to be used as a local anesthetic and as an intermediate for the production of other derivatives.
Example: A mixture of 20 parts by weight of acrylic acid (2-chloro-6-methyl-anilide), 18 parts by weight of 2-methyl 1-piperidine and a few drops of trimethylbenzyl ammonium hydroxide is heated to 145 in an autoclave for 20 hours. After cooling, steam is passed through the reaction mixture for the purpose of removing volatile components. It is then evaporated and the residue is recrystallized from petroleum ether.
The ss- (2'-methyl-piperidino) -propionic acid-2-chloro-6-methyl-anilide is thus obtained as a colorless crystal powder.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311581T | 1952-02-25 | ||
| CH306512T | 1952-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311581A true CH311581A (en) | 1955-11-30 |
Family
ID=25735180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311581D CH311581A (en) | 1952-02-25 | 1952-02-25 | Process for the preparation of a basic substituted fatty acid (2-halogen-6-methyl-anilide). |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH311581A (en) |
-
1952
- 1952-02-25 CH CH311581D patent/CH311581A/en unknown
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