CH242289A - 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
- CH242289A CH242289A CH242289DA CH242289A CH 242289 A CH242289 A CH 242289A CH 242289D A CH242289D A CH 242289DA CH 242289 A CH242289 A CH 242289A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- cycloalkyl
- aryl
- preparation
- ester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 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 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- -1 haloalkyl ester Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines basischen Esters einer 1-Aryl-cycloalkyl-l-carbonsäure. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines basischen Esters einer 1-Aryl-cycloalkyl-l- carbonsäure. Das Verfahren ist dadurch ge kennzeichnet, dass man ein ss-Halogen-äthanol auf eine Verbindung der Formel
EMI0001.0008
worin g einen bei der Reaktion sich abspal tenden Rest bedeutet, gegebenenfalls in Ge genwart eines Kondensationsmittels,
einwir ken lässt und anschliessend den erhaltenen Halogenalkylester mit Diäthylamin umsetzt.
Der 1-Phenyl-cyclopentyl-l-carbonsäure- diäthyl-aminoäthanolester bildet eine farblose Flüssigkeit vom Siedepunkt 112-115 unter 0,07 mm, sein Hydrochlorid schmilzt bei 145 bis 146 . Die neue Verbindung soll therapeutische Verwendung finden.
<I>Beispiel:</I> 38 Teile 1-Phenyl-cyclopentyl-l-carbon- säure werden mit Thionylchlorid in üblicher Weise in das Säurechlorid übergeführt und dieses mit 16 Teilen Äthylenchlorhydrin in 150 Teilen Pyridin umgesetzt. Nach be endeter Reaktion giesst man in Wasser, stellt kongosauer und äthert aus. Nach dem Wa schen und Trocknen der Ätherlösung wird das Lösungsmittel abdestilliert und der Rück stand imVakuum fraktioniert.
Der 1-Phenyl- cyclopentyl-l-carbonsäure--ss-chloräthylester siedet bei 110-115 unter 0,02 mm. 25 Teile dieser Verbindung setzt man in der Wärme mit 15 Teilen Diäthylamin um, nimmt nach beendeter Reaktion in verdünnter Salzsäure auf,
äthert aus und gewinnt aus der wässrigen Lösung den basischen Ester durch Zugabe von Pottasche und Ausäthern. Nach Waschen und Trocknen der Ätherlösung wird das Lö- sungsmittel abdestilliert und der Rückstand im Hochvakuum fraktioniert. Die neue Ver- bindung siedet bei 112-115 unter 0,07 mm.
Process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. The subject of the present additional patent is a process for the preparation of a basic ester of a 1-aryl-cycloalkyl-1-carboxylic acid. The process is characterized in that an β-haloethanol is applied to a compound of the formula
EMI0001.0008
where g denotes a radical which is split off during the reaction, optionally in the presence of a condensing agent,
einwir ken and then reacting the haloalkyl ester obtained with diethylamine.
The 1-phenyl-cyclopentyl-1-carboxylic acid diethyl aminoethanol ester forms a colorless liquid with a boiling point of 112-115 below 0.07 mm; its hydrochloride melts at 145 to 146. The new compound should find therapeutic use.
<I> Example: </I> 38 parts of 1-phenyl-cyclopentyl-l-carboxylic acid are converted into the acid chloride with thionyl chloride in the usual way and this is reacted with 16 parts of ethylene chlorohydrin in 150 parts of pyridine. When the reaction has ended, it is poured into water, made Congo acidic and etherified. After washing and drying the ethereal solution, the solvent is distilled off and the residue is fractionated in vacuo.
The 1-phenyl-cyclopentyl-1-carboxylic acid - ss-chloroethyl ester boils below 0.02 mm at 110-115. 25 parts of this compound are reacted with 15 parts of diethylamine in the heat, and when the reaction is complete it is taken up in dilute hydrochloric acid,
ethers out and extracts the basic ester from the aqueous solution by adding potash and ethers. After washing and drying the ethereal solution, the solvent is distilled off and the residue is fractionated in a high vacuum. The new compound boils below 0.07 mm at 112-115.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH242289T | 1942-12-16 | ||
| CH234452T | 1944-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH242289A true CH242289A (en) | 1946-04-30 |
Family
ID=25727875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH242289D CH242289A (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) | CH242289A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1005973B (en) * | 1953-06-26 | 1957-04-11 | Henri Morren | Process for the production of new spasmolytically effective basic esters |
-
1942
- 1942-12-16 CH CH242289D patent/CH242289A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1005973B (en) * | 1953-06-26 | 1957-04-11 | Henri Morren | Process for the production of new spasmolytically effective basic esters |
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