CH192994A - Process for the preparation of diphenylacetic acid-2-allylethylaminoethanol ester. - Google Patents
Process for the preparation of diphenylacetic acid-2-allylethylaminoethanol ester.Info
- Publication number
- CH192994A CH192994A CH192994DA CH192994A CH 192994 A CH192994 A CH 192994A CH 192994D A CH192994D A CH 192994DA CH 192994 A CH192994 A CH 192994A
- Authority
- CH
- Switzerland
- Prior art keywords
- allylethylaminoethanol
- ester
- diphenylacetic acid
- preparation
- acid
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 claims description 5
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- -1 hydrochloric acid ester Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Diphenylessigsäure-2-allyläthylarninoäthanolester. Es wurde gefunden, dass man zu dem im Patent Nr.1914,64 beschriebenen Diphenyl- essigsä.ure-2-a.llyläthylaminoäthanolester ge langen kann, wenn man auf ein Metallsalz der Diphenylessigsäure einen reaktionsfähi gen Ester des 2-Allyläthylaminoäthanols einwirken lässt.
Die Verbindung soll therapeutische Ver wendung finden. Beispiel: 21 Teile D.iphenylessigsäure, 20 Teile Chloräthylallyläthylamin-hydrochlorid (dar gestellt aus Allyläthylaminoäthanol und Thionylehlorid), 2,5 Teile Kaliumcarbonat und 100 Teile Aceton werden am R,ückfluss bis zur beendeten Reaktion gekocht. Nach dem Abkühlen wird filtriert, mit Aceton ge waschen und das eingedampfte Filtrat in Äther aufgenommen.
Die Atherlösung wird mit verdünnter Natriumcarbonatlösung ge waschen und über Kaliumearbonat getrock net. Nach dem Verdampfen des Äthers er- hält man den Diphenylessigsäure-2-allyl- ätliylaminoäthanolester als 01, das im Hoch vakuum fraktioniert werden kann.
Dieselbe Verbindung kann auch gewonnen werden, wenn man zum Beispiel an Stelle von Kaliumcarbonat ein anderes AlkaIi- carbonat verwendet, oder wenn man ein fer tiges Alkali- oder anderes Metallsalz der Diphenylessigsäure mit Chloräthylallyläthyl- ämin umsetzt.
Statt diesem können auch Ester des Allyläthylaminoäthanols mit an dern Halogenwasserstoffsäuren oder zuin Beispiel mit Arylsulfonsäuren wie Toluol- sulfonsäure verwendet werden.
Process for the preparation of diphenylacetic acid-2-allyläthylarninoäthanolester. It has been found that the diphenyl acetic acid-2-a.
The compound is intended to find therapeutic use. Example: 21 parts of diphenylacetic acid, 20 parts of chloroethylallylethylamine hydrochloride (is made from allylethylaminoethanol and thionyl chloride), 2.5 parts of potassium carbonate and 100 parts of acetone are boiled on reflux until the reaction is complete. After cooling, it is filtered, washed with acetone and the filtrate which has evaporated is taken up in ether.
The ether solution is washed ge with dilute sodium carbonate solution and getrock net over potassium carbonate. After evaporation of the ether, the diphenylacetic acid-2-allyl-ätliylaminoäthanolester is obtained as 01, which can be fractionated in a high vacuum.
The same compound can also be obtained if, for example, another alkali carbonate is used instead of potassium carbonate, or if a finished alkali or other metal salt of diphenylacetic acid is reacted with chloroethylallylethylamine.
Instead of this, esters of allylethylaminoethanol can also be used with other hydrohalic acids or, for example, with arylsulfonic acids such as toluenesulfonic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH183065T | 1934-07-12 | ||
| CH192994T | 1934-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH192994A true CH192994A (en) | 1937-09-15 |
Family
ID=25720823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH192994D CH192994A (en) | 1934-07-12 | 1934-07-12 | Process for the preparation of diphenylacetic acid-2-allylethylaminoethanol ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH192994A (en) |
-
1934
- 1934-07-12 CH CH192994D patent/CH192994A/en unknown
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