CH311678A - 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
- CH311678A CH311678A CH311678DA CH311678A CH 311678 A CH311678 A CH 311678A CH 311678D A CH311678D A CH 311678DA CH 311678 A CH311678 A CH 311678A
- Authority
- CH
- Switzerland
- Prior art keywords
- diethylamine
- ethyl
- methyl
- fatty acid
- methoxyphenoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 7
- 239000000194 fatty acid Substances 0.000 title claims description 7
- 229930195729 fatty acid Natural products 0.000 title claims description 7
- 150000004665 fatty acids Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000003589 local anesthetic agent Substances 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- UGYQLLBBRLDEHY-UHFFFAOYSA-N 2-(diethylamino)propanamide Chemical group CCN(CC)C(C)C(N)=O UGYQLLBBRLDEHY-UHFFFAOYSA-N 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012230 colorless oil Substances 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000012259 ether extract Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 229940072033 potash Drugs 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides.
Gegenstand des vorliegenden Patentes bil clet ein Verfahren zur Herstellung eines neuen basiseh substituierten Fettsäureamides, welches dadureh gekennzeichnet ist, dass man eine Verbindung der Formel
EMI1.1
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Diäthylamin 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 Alkylsulfonyloxy-oder Arylsulfonyloxygruppe, beste hen. Der Austausch der Gruppe X gegen den Diäthylaminrest erfolgt z. B. durch einfaches Erwärmen mit Diäthylamin, gegebenenfalls in Gegenwart eines basisch reagierenden Kondensationsmittels, oder von Diäthylamin im Überschuss. Das N- [2- (3'-Methoxy-phenoxy)- äthyl-1]-N-methyl-diäthylaminoaeetamid ist ein farbloses, unter 0,06 mm bei 157-158 siedendes 01.
Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden.
Beispiel :
25,8 g N- [2- (3'-Methoxy-phenoxy)-äthyl-1]- N-methyl-ehloraeeta, mid und 22 g Diäthylamin werden zusammen in 150 mS abs. Benzol 6 Stunden auf dem Wasserbad erhitzt. Das Re aktionsgemisch h wird mit Wasser ausgeschüt- telt und dann mit 2n-Salzsäure ausgezogen.
Darauf wird der salzsaure Auszug mit Äther extrahiert, unter Eiskühlung mit konz. Natronlauge versetzt und das ausgesehiedene öl in Äther aufgenommen. Nach dem Trocknen der Ätherauszüge über Pottasche wird der Äther verdampft und der Rüekstand im Hochvakuum destilliert.
Dabei gewinnt man das unter 0,06 min bei 157-158 siedende N- [2- (3'-Methoxy-phen oxy)-äthyl-1]-N-methyl-diäthylaminoacetamid als farbloses, säurelösliches 01.
PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, da dureh gekennzeichnet, dass man eine Verbindung der Formel
EMI1.2
in welcher X einen reaktionsfähigen, wahrend der Reaktion sich abspaltenden Rest bedeutet, mit Diäthylamin umsetzt. Das auf diese Weise erhaltene N- [2- (3'-Methoxy-phenoxy)-äthyl 1]-N. methyl-diäthylaminoacetamid bildet ein farbloses, unter 0,06 mm bei 157-158 siedendes 01.
Das neue Amid soll als Lokalanästhetikum und als Zwisehenprodukt Verwendung finden.
UNTERANSPRUCH :
Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein N- [2- (3'-Methoxy phenoxy)-äthyl-1]-N-methyl-halogen-acetamid mit Diäthylamin reagieren lässt.
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the production of a new basic substituted fatty acid amide.
The subject of the present patent bil clet a process for the preparation of a new basic substituted fatty acid amide, which is characterized by the fact that a compound of the formula
EMI1.1
in which X is a reactive radical which is split off during the reaction, is reacted with diethylamine.
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 alkylsulfonyloxy or arylsulfonyloxy group, best hen. The exchange of group X against the diethylamine residue takes place z. B. by simply heating with diethylamine, optionally in the presence of a basic condensing agent, or diethylamine in excess. The N- [2- (3'-methoxyphenoxy) - ethyl-1] -N-methyl-diethylaminoaetamide is a colorless oil that boils below 0.06 mm at 157-158.
The new amide will be used as a local anesthetic and as an intermediate for the production of other derivatives.
Example:
25.8 g of N- [2- (3'-methoxyphenoxy) ethyl-1] - N-methyl-ehloraeeta, mid and 22 g of diethylamine are dissolved together in 150 mS abs. Benzene heated on a water bath for 6 hours. The reaction mixture h is extracted by shaking with water and then extracted with 2N hydrochloric acid.
The hydrochloric acid extract is then extracted with ether, with conc. Sodium hydroxide solution was added and the separated oil was absorbed in ether. After the ether extracts have dried over potash, the ether is evaporated and the residue is distilled in a high vacuum.
The N- [2- (3'-methoxyphenoxy) -ethyl-1] -N-methyl-diethylaminoacetamide, which boils at 157-158 for less than 0.06 min, is obtained as colorless, acid-soluble oil.
PATENT CLAIM:
Process for the preparation of a new basic substituted fatty acid amide, characterized by the fact that one is a compound of the formula
EMI1.2
in which X is a reactive radical which is split off during the reaction, reacts with diethylamine. The N- [2- (3'-methoxyphenoxy) ethyl 1] -N obtained in this way. methyl-diethylaminoacetamide forms a colorless 01 boiling below 0.06 mm at 157-158.
The new amide is to be used as a local anesthetic and as an intermediate product.
SUBClaim:
Process according to patent claim, characterized in that an N- [2- (3'-methoxy phenoxy) ethyl-1] -N-methyl-haloacetamide is allowed to react with diethylamine.
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311678T | 1952-06-08 | ||
| CH307799T | 1952-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311678A true CH311678A (en) | 1955-11-30 |
Family
ID=25735411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311678D CH311678A (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) | CH311678A (en) |
-
1952
- 1952-06-08 CH CH311678D patent/CH311678A/en unknown
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