CH311557A - 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
- CH311557A CH311557A CH311557DA CH311557A CH 311557 A CH311557 A CH 311557A CH 311557D A CH311557D A CH 311557DA CH 311557 A CH311557 A CH 311557A
- Authority
- CH
- Switzerland
- Prior art keywords
- fatty acid
- substituted fatty
- production
- acid amide
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 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
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 6
- -1 2-methyl-piperidinoacetic acid halide Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- IZYFKLAMVLELBP-UHFFFAOYSA-N 2-(2-methylpiperidin-1-ium-1-yl)acetate Chemical compound CC1CCCCN1CC(O)=O IZYFKLAMVLELBP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- YTWYJCFQNOZVEC-UHFFFAOYSA-N 2-piperidin-1-ium-1-ylpropanoate Chemical compound OC(=O)C(C)N1CCCCC1 YTWYJCFQNOZVEC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Description
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines netten basisch substituierten Fettsäureamides, wel- elies dadureh gekennzeichnet ist, dass man auf eine Verbindunz der Formel.
EMI0001.0009
eine Verbindung der Formel
EMI0001.0010
in welchen Formeln X und Y reaktionsfähige, bei der Reaktion sich abspaltende Reste be deuten, einwirken lässt.
Als Verbindungen der Formel T kommen für einen Umsatz beispielsweise in Frage: Das freie Amin (Y = H), aber auch dessen Salze, wie beispielsweise das Hydrochlorid oder das Sulfat.
Als Verbindungen der Formel 11 kommen beispielsweise in Frage: 2-Methyl-piperidino- essigsäure selbst und ihre reaktionsfähigen funktionellen Derivate wie ihre Halogenide, ihre Ester, ihre Anhydride, beispielsweise die reinen und auch die gemischten Anhydride mit Phosphorsäure, Schwefelsäure und Koh lensäure usf.
Man kann beispielsweise N-[2-(2',4',6'-Tri- metliyl-phenoxy)-äthyl-1]-methylamin oder auch ein Salz desselben in Gegenwart eines für diese Zwecke geeigneten wasserabspalten den Mittels wie Phosphorpentoxyd, Phosphor oxyehlorid usf. mit 2-Methyl-piperidinoessig- säure behandeln.
Weiter kann man auch N-[2-(2',4',6'-Tri- methyl - phenoxy) - äthyl -1 ] - methylamin bzw. ein Salz desselben mit einem 2-Methyl-piperi- dinoessigsäitrehalogenid (bzw. einem Salz eines solchen) oder einem Anhydrid zur Re aktion bringen.
Es ist weiterhin auch möglich, N-[2-(2',4', 6'- Trimethyl - phenoxy) -äthyl-1 ] -methylamin mit einem 2-Methyl-piperidinoessigsäureester, vorzugsweise einem Arylester, bei erhöhter Temperatur zu acylieren.
Das auf diese Weise erhaltene a-Methyl- piperidinoessigsäure-N- [2- (2',4',6'- trimethyl- phenoxy)-äthyl-1]-methylamid bildet einfarb loses, unter 0,02 mm bei 170-171 sieden des öl.
Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung wei terer Derivate Verwendung finden.
Beispiel: <I>-</I> 19,3 g N-[2-(2',4',6'-Trimethyl-phenoxy)- äthyl-1 ] -methylamin in Benzol werden mit einer Mischung von 21,2 g 2-Methyl-piperi- dinoessigsäurechlorid-hydrochlorid und 20,2 g Triäthylamin erwärmt. Anschliessend wird das gebildete Triäthylaminhydrochlorid durch Ausschütteln mit Wasser entfernt, die Benzol lösung nach dem Trocknen verdampft und der Rückstand im Hochvakuum destilliert.
Man erhält so in guter Ausbeute das a-Me- thyl - piperidinoessigsäure -N - [2 - (2',4',6'-tri- methyl - phenoxy) - äthyl -1 ] - methylamid, wel ches ein unter 0,02 mm bei 170-171. sieden des farbloses Öl darstellt.
Die- Reaktion kann auch ohne Verdün- niuigs-und Kondensationsmittel durchgeführt werden, indem man beispielsweise das 2-Me- thyl-piperidinoessigsäurechlorid-hydrochlorid mit N-[2-(2',4',6'-Trimethyl-phenoxy)-äthyl- 1]-methylamin trocken erhitzt, anschliessend die Reaktionsmasse mit Wasser verdünnt und in üblicher Weise aufarbeitet.
Process for the production of a new basic substituted fatty acid amide. The subject matter of the present patent is a process for the preparation of a nice, basic substituted fatty acid amide, which is characterized by the fact that a compound of the formula
EMI0001.0009
a compound of the formula
EMI0001.0010
in which formulas X and Y are reactive residues that are split off during the reaction.
Compounds of the formula T which can be used for a conversion are, for example: The free amine (Y = H), but also its salts, such as the hydrochloride or the sulfate.
Examples of possible compounds of formula 11 are: 2-methylpiperidinoacetic acid itself and its reactive functional derivatives such as its halides, its esters, its anhydrides, for example the pure and also the mixed anhydrides with phosphoric acid, sulfuric acid and carbon acid, etc.
For example, N- [2- (2 ', 4', 6'-trimethyl-phenoxy) -ethyl-1] -methylamine or a salt thereof in the presence of a dehydrating agent suitable for this purpose such as phosphorus pentoxide, phosphorus Treat oxyehloride etc. with 2-methyl-piperidinoacetic acid.
In addition, N- [2- (2 ', 4', 6'-trimethyl-phenoxy) -ethyl -1] -methylamine or a salt thereof with a 2-methyl-piperidinoacetic acid halide (or a Salt of such) or an anhydride to react.
It is furthermore also possible to acylate N- [2- (2 ', 4', 6'-trimethyl-phenoxy) -ethyl-1] -methylamine with a 2-methylpiperidinoacetic acid ester, preferably an aryl ester, at elevated temperature.
The a-methylpiperidinoacetic acid-N- [2- (2 ', 4', 6'-trimethylphenoxy) -ethyl-1] -methylamide obtained in this way forms a colorless, less than 0.02 mm at 170-171 boiling the oil.
The new amide is to be used as a local anesthetic and as an intermediate for the production of further derivatives.
Example: <I> - </I> 19.3 g of N- [2- (2 ', 4', 6'-trimethyl-phenoxy) -ethyl-1] -methylamine in benzene are mixed with a mixture of 21.2 g of 2-methyl-piperidinoacetic acid chloride hydrochloride and 20.2 g of triethylamine were heated. The triethylamine hydrochloride formed is then removed by shaking with water, the benzene solution is evaporated after drying and the residue is distilled in a high vacuum.
The α-methyl piperidinoacetic acid -N - [2 - (2 ', 4', 6'-trimethyl-phenoxy) -ethyl-1] -methylamide, which is one below 0, is obtained in good yield. 02 mm for 170-171. represents boiling of the colorless oil.
The reaction can also be carried out without diluents and condensation agents, for example by converting the 2-methylpiperidinoacetic acid chloride hydrochloride with N- [2- (2 ', 4', 6'-trimethylphenoxy) ethyl - 1] -methylamine heated dry, then diluted the reaction mass with water and worked up in the usual way.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311557T | 1952-06-08 | ||
| CH306201T | 1955-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311557A true CH311557A (en) | 1955-11-30 |
Family
ID=25735084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311557D CH311557A (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) | CH311557A (en) |
-
1952
- 1952-06-08 CH CH311557D patent/CH311557A/en unknown
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