CH240161A - Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. - Google Patents
Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid.Info
- Publication number
- CH240161A CH240161A CH240161DA CH240161A CH 240161 A CH240161 A CH 240161A CH 240161D A CH240161D A CH 240161DA CH 240161 A CH240161 A CH 240161A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- marked
- phenyl
- carboxylic acid
- cyclopentyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 230000000694 effects Effects 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- -1 1-phenyl-cyclopentyl Chemical group 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical group CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Darstellung eines basischen Esters einer 1-Aryl-cycloalkyl-l-earbonsänre. Gegenstand des vorliegenden Zusatzpaten- tes ist ein Verfahren zur Darstellung eines basischen Esters einer 1-Aryl-cycJoalkyl-l- carbonsäure. Das Verfahren ist dadurch ge- kennzeichnet,
dass man Dimethylaminoätha- nol auf eine Verbindung der Formel
EMI0001.0015
worin X einen bei der Reaktion sich abspal tenden Rest bedeutet, gegebenenfalls in Ge genwart eines Kondensationsmittels; einwir ken lässt. Der 1-Phenyl-cyclopentyl-l-carbonsäure- dimethylaminoäthano,l-ester bildet eine farb lose Flüssigkeit vom Siedepunkt 114-115 unter 0,15 mm.
Die neue Verbindung soll therapeutische Verwendung finden. <I>Beispiel:</I> 19 Teile 1-Phenyl-.oyclapentyl-l-carbon- säure werden mit Thionylchlorid in üblicher Weise in das Säurechlorid übergeführt und dieses in 200 Teilen absolutem Benzol gelöst. Unter Rühren tropft man eine Lösung von 8,
9 Teilen Dimethydaminoäth@auol in 50 Tei len absolutem Benzol zu und erwärmt an schliessend 2 Stunden zum Sieden. Man schüttelt zweimal mit Wasser und einmal mit verdünnter Salzsäure aus.
Die vereinigten wässrigen Lösungen werden, ausgeäthert, dne Base mit Pottasche in Freiheit gesetzt und in Äther aufgenommen. Die ätherische Lösung wird mit Wasser gewaschen,
über Pottasche getrocknet und das Lösungsmittel abdestil- liert. Die neue Verbindung siedet bei 114 biss 115 unter 0,15 mm.
An Stelle des Säurechlorids können auch andere Halogenide der 1-Phenyl-cyclopentyl- 1-carbonsäure, die Säure selbst, ihre Ester oder ihr Anhydrid verwendet werden.
Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. The subject matter of the present additional patent is a process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. The procedure is characterized by
that you dimethylaminoethanol on a compound of the formula
EMI0001.0015
where X is a radical which splits off during the reaction, optionally in the presence of a condensing agent; has an effect. The 1-phenyl-cyclopentyl-l-carboxylic acid dimethylaminoethano, l-ester forms a colorless liquid with a boiling point of 114-115 below 0.15 mm.
The new compound should find therapeutic use. <I> Example: </I> 19 parts of 1-phenyl-.oyclapentyl-1-carboxylic acid are converted into the acid chloride with thionyl chloride in the usual way and this is dissolved in 200 parts of absolute benzene. A solution of 8 is added dropwise while stirring
9 parts of dimethydaminoeth @ auol in 50 parts of absolute benzene and then heated to the boil for 2 hours. It is extracted twice with water and once with dilute hydrochloric acid.
The combined aqueous solutions are etherified, the base is set free with potash and taken up in ether. The ethereal solution is washed with water,
dried over potash and the solvent was distilled off. The new compound boils below 0.15 mm at 114 to 115.
Instead of the acid chloride, it is also possible to use other halides of 1-phenyl-cyclopentyl-1-carboxylic acid, the acid itself, its esters or its anhydride.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH240161T | 1942-12-16 | ||
| CH234452T | 1944-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH240161A true CH240161A (en) | 1945-11-30 |
Family
ID=25727864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240161D CH240161A (en) | 1942-12-16 | 1942-12-16 | Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH240161A (en) |
-
1942
- 1942-12-16 CH CH240161D patent/CH240161A/en unknown
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