CH240163A - 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
- CH240163A CH240163A CH240163DA CH240163A CH 240163 A CH240163 A CH 240163A CH 240163D A CH240163D A CH 240163DA CH 240163 A CH240163 A CH 240163A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- propanol
- phenyl
- act
- cyclopentyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 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
- 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
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000203 mixture Substances 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)
Description
Verfahren zier Darstellung eines basischen Esters einer 1-Aryl-ssyeloallzyl-l-earbonsäure. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines baeisehen Esters einer 1-Aryl-cycloalkyl-l- carbonsäure. Das Verfahren ist dadurch ge kennzeichnet"dass man y-Dimethylamino-pro- panol auf eine Verbindung der Formel
EMI0001.0014
worin X einen bei der
Reaktionsich abspgl- tend#en Rest bedeutet, gegebenenfalls in Ge genwart eines Kondensationsmittels, einwir ken lässt.
Der 1-Phenyl=evclopentyl-l-carbonsäure- y-,dim-ethyllamino-propanolester bildet eine farblose Flüssigkeit vom Siedepunkt 125 bis 127 unter 0,25 mm, sein Hydrochlorid schmilzt bei 147-148 .
Die neue Verbindung soll therapeutische Verwendung finden, Beispiel: 19 Teile 1-Phenyl,cyclopentyl-l-carbon- säure werdIen mit Thionylchlorid in üblicher Weise in das Säurechlorid übergeführt und dieses in 200 Teilen absolutem Benzol gelöst. Unter Rühren tropft man eine Lösung von 10,3 Teilen y-Dimethylamino-proponal in 50 Teilen absolutem Benzol zu und erwärmt anschliessend 2 Stunden zum Sieden.
Man schüttelt zweianal mit Wasser und einmal mit verdünnter Salzsäure aus. Die vereinigten wässrigen Lösungen werden ausgeäthert, die Base mit Pottasche in Freiheit gesetzt und in Äther aufgenommen. Die ätherische Lö sung wird mit Wasser gewaschen, über Pott asche getrocknet und das Lösungsmittel ab destilliert. Die neue Verbindung siedet bei 125-127 unter 0,25 mm, ihr Hydrochlorid schmilzt bei 147-148 .
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-ssyeloallzyl-1-carboxylic acid. The subject of the present additional patent is a process for the preparation of an basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. The process is characterized in that γ-dimethylaminopropanol is applied to a compound of the formula
EMI0001.0014
where X is one of the
Reaction-expressing radical means, optionally in the presence of a condensing agent, allowed to act.
The 1-phenyl = evclopentyl-1-carboxylic acid y-, dim-ethyllamino-propanol ester forms a colorless liquid with a boiling point of 125 to 127 below 0.25 mm, its hydrochloride melts at 147-148.
The new compound is intended to be used therapeutically, for example: 19 parts of 1-phenyl, cyclopentyl-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 10.3 parts of γ-dimethylaminoproponal in 50 parts of absolute benzene is added dropwise with stirring and the mixture is 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 extracted with ether, the base is released with potash and taken up in ether. The ethereal solution is washed with water, dried over pot ash and the solvent is distilled off. The new compound boils below 0.25 mm at 125-127, its hydrochloride melts at 147-148.
Instead of the acid chloride, other halides of 1-phenyl-cyclopentyl-1-carboxylic acid, the acid itself, its ester or its anhydride can also be used.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH240163T | 1942-12-16 | ||
| CH234452T | 1944-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH240163A true CH240163A (en) | 1945-11-30 |
Family
ID=25727866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240163D CH240163A (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) | CH240163A (en) |
-
1942
- 1942-12-16 CH CH240163D patent/CH240163A/en unknown
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