CH312690A - Process for the preparation of a basic substituted fatty acid amide - Google Patents
Process for the preparation of a basic substituted fatty acid amideInfo
- Publication number
- CH312690A CH312690A CH312690DA CH312690A CH 312690 A CH312690 A CH 312690A CH 312690D A CH312690D A CH 312690DA CH 312690 A CH312690 A CH 312690A
- Authority
- CH
- Switzerland
- Prior art keywords
- diethylamine
- preparation
- acetaminophenoxy
- propyl
- ether
- Prior art date
Links
- 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
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000155 melt Substances 0.000 claims description 6
- 229940075930 picrate Drugs 0.000 claims description 6
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 claims description 6
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000003589 local anesthetic agent Substances 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000203 mixture 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
- 125000001453 quaternary ammonium 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
- 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 basisch substituierten Fettsäureamides
Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides, welehes dadurch gekennzeichnet ist, dass man eine Verbindung der Formel
EMI1.1
mit Diäthylamin umsetzt. Die Umsetzung kann in An-oder Abwesenheit von Lösungs-bzw.
Verdünnungsmitteln und Anlagerungskatalysatoren erfolgen. Vorzugsweise wird wegen der Leichtflüchtigkeit des Diäthylamins unter Druek gearbeitet. Als Anlagerungskatalysatoren benützt man vorteilhaft quaternäre Ammoniumbasen, wie z. B. Trimethylbenzyl ammoniumhydroxyd.
Das so erhaltene S-Diäthylamino-propion- säure-N- (3-o-acetamino-phenoxy-propyl-2)- methylamid ist eine farblose, zähflüssige Masse.
Das Pikrat der Base schmilzt bei 125-126 .
Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden.
Beispiel
Ein Gemisch von 16, 5 g Acrylsäure-N- (3- O - acetamino - phenoxy - propyl-2) - methylamid, 22, 0 g Diäthylamin und einigen Tropfen Tri methyl-benzylammoniumhydroxyd wird im Autoklaven während einigen Stunden auf 1450 erhitzt. Das überschüssige Diäthylamin wird abdestilliert, der Rüekstand in. Äther auf- genommen und mit 2n-Salzsäure ausgezogen.
Der salzsaure Auszug wird gut mit Ather gewaschen und dann mit konzentrierter Lauge alkalisiert, wobei sich ein 61 ausscheidet, welches in Äther aufgenommen wird. Nach dem Trocknen über Pottasche wird der ¯ther verdampft und der Rüekstand im Hochvakuum getrocknet. Man gewinnt so das fl- Diäthylamino-propionsäure-N- (3-o-acetamino- phenoxy-propyl-2)-methylamid als farblose zähflüssige Masse. Das Pikrat der Base schmilzt bei 125-126 .
PATENTANSPRUCH
Verfahren zur Herstellung eines basisch substituierten Fettsäureamides, dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.2
mit Diäthylamin umsetzt. Das so erhaltene 8- Diäthylamino-propionsäure-N- (3-o-acetamino- phenoxy-propyl-2)-methylamid ist eine farblose, zÏhfl ssige Masse. Das Pikrat der Base schmilzt bei 125-126 .
Es soll als Lokalanästhetikum und als Zwi schenprodukt Verwendung finden.
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of a basic substituted fatty acid amide
The subject of the present patent forms a process for the preparation of a new basic substituted fatty acid amide, which is characterized in that a compound of the formula
EMI1.1
Reacts with diethylamine. The implementation can in the presence or absence of solution or.
Diluents and addition catalysts take place. Because of the volatility of diethylamine, it is preferable to work under pressure. As addition catalysts, it is advantageous to use quaternary ammonium bases, such as. B. trimethylbenzyl ammonium hydroxide.
The S-diethylamino-propionic acid-N- (3-o-acetaminophenoxy-propyl-2) -methylamide obtained in this way is a colorless, viscous mass.
The picrate of the base melts at 125-126.
The new amide will be used as a local anesthetic and as an intermediate for the production of other derivatives.
example
A mixture of 16.5 g of acrylic acid-N- (3-O-acetaminophenoxy-propyl-2) -methylamide, 22.0 g of diethylamine and a few drops of tri-methylbenzylammonium hydroxide is heated to 1450 in the autoclave for a few hours. The excess diethylamine is distilled off, the residue is taken up in ether and extracted with 2N hydrochloric acid.
The hydrochloric acid extract is washed well with ether and then made alkaline with concentrated lye, whereupon a 61 is precipitated which is taken up in ether. After drying over potash, the ether is evaporated and the residue is dried in a high vacuum. The fl-diethylamino-propionic acid-N- (3-o-acetaminophenoxy-propyl-2) -methylamide is obtained as a colorless, viscous mass. The picrate of the base melts at 125-126.
PATENT CLAIM
Process for the preparation of a basic substituted fatty acid amide, characterized in that a compound of the formula
EMI1.2
Reacts with diethylamine. The 8-diethylamino-propionic acid-N- (3-o-acetaminophenoxy-propyl-2) -methylamide obtained in this way is a colorless, viscous mass. The picrate of the base melts at 125-126.
It should be used as a local anesthetic and as an intermediate product.
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH312690T | 1952-06-08 | ||
| CH306512T | 1952-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH312690A true CH312690A (en) | 1956-02-15 |
Family
ID=25735188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH312690D CH312690A (en) | 1952-06-08 | 1952-06-08 | Process for the preparation of a basic substituted fatty acid amide |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH312690A (en) |
-
1952
- 1952-06-08 CH CH312690D patent/CH312690A/en unknown
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