CH183065A - Process for the preparation of benzilic acid-2-diethylaminoethanol ester. - Google Patents
Process for the preparation of benzilic acid-2-diethylaminoethanol ester.Info
- Publication number
- CH183065A CH183065A CH183065DA CH183065A CH 183065 A CH183065 A CH 183065A CH 183065D A CH183065D A CH 183065DA CH 183065 A CH183065 A CH 183065A
- Authority
- CH
- Switzerland
- Prior art keywords
- ester
- diethylaminoethanol
- benzilic acid
- acid
- act
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Benzilsäure-2-diäthylaniinoäthanolester. Es wurde gefunden, dass man zu Benzil- säure-2-diäthylamino-ätlianolester gelangen kann, wenn man auf ein Metallsalz der Ben- zilsäure einen reaktionsfähigen Ester des 2-Diäthy laininoäthanols einwirken lässt.
Der so erhaltene Benzilsäure-2-diätliyl- aniinoäthanolester siedet bei 1.49 bis 151 unter<B>0,01</B> mm Druck. Er schmilzt bei 51 bis 52 und kann aus Petroläther um kristallisiert werden. Sein Hydrochlorid zeigt den F.<B>170</B> bis 1701/, . Sein Jodmethylat bildet Kristalle vom F.<B>137</B> bis 138 . Sein Chlorinelbvl@it ist in Wasser sehr leicht lös lich; es kann aus absolutem Alkohol und Essigester umkristallisiert werden und schmilzt bei 185 .
Die neue Verbindung soll therapeutische Verwendung finden.
Beispiel: 3,4 Teile Benzilsäure und 3 Teile Chlor- äthyldiäthylaminhydrochlorid werden in 9 Teilen Aceton mit 4 Teilen trockenem pul- verisiertem Kaliumkarbonat mehrere Stun den am Rückflusskühler gekocht. Nach be endeter Reaktion wird gekühlt, abgenutscht und der Filterrückstand mit Aceton ausge waschen.
Das Filtrat wird eingedampft, das zurückbleibende 01 in Äther aufgenommen, die ätherische Lösung mit verdünnter Na triumkarbonatlösung geschüttelt, der Äther auszug über Kaliumkarbonat getrocknet und das Lösungsmittel verdampft. Der zurück bleibende Benzilsäure-2-diäthylaminoäthanol- ester wird im Vakuumdestilliert.
Dieselbe Verbindung kann auch gewon nen werden, wenn man zum Beispiel an Stelle von Kaliumkarbonat ein anderes Alkalikar- bonat verwendet, oder wenn man ein fertiges Alkali- oder anderes Metallsalz der Benzil- säure mit Chloräthyldiäthylamin umsetzt.
Statt diesem können auch Ester des Di- äthylaminoäthanols mit andern Flalogen- wasserstoffsäuren oder zum Beispiel mit Arylsulfonsäuren, wie Toluolsulfonsäure, verwendet werden.
Process for the preparation of benzilic acid-2-diethylaniinoethanol ester. It has been found that benzilic acid-2-diethylamino-ethyl-anol ester can be obtained if a reactive ester of 2-diethylamino-ethanol is allowed to act on a metal salt of benzilic acid.
The benzilic acid-2-diethylaniinoethanol ester thus obtained boils at 1.49 to 151 under <B> 0.01 </B> mm pressure. It melts at 51 to 52 and can be crystallized from petroleum ether. Its hydrochloride shows the F. <B> 170 </B> to 1701 /,. Its iodine methylate forms crystals from F. <B> 137 </B> to 138. Its chlorine content is very easily soluble in water; it can be recrystallized from absolute alcohol and ethyl acetate and melts at 185.
The new compound should find therapeutic use.
Example: 3.4 parts of benzilic acid and 3 parts of chloroethyl diethylamine hydrochloride are boiled in 9 parts of acetone with 4 parts of dry powdered potassium carbonate for several hours on the reflux condenser. When the reaction has ended, it is cooled, suction filtered and the filter residue is washed out with acetone.
The filtrate is evaporated, the remaining oil is taken up in ether, the ethereal solution is shaken with dilute sodium carbonate solution, the ether extract is dried over potassium carbonate and the solvent is evaporated. The remaining benzilic acid 2-diethylaminoethanol ester is distilled in vacuo.
The same compound can also be obtained if, for example, another alkali metal carbonate is used instead of potassium carbonate, or if a finished alkali or other metal salt of benzilic acid is reacted with chloroethyl diethylamine.
Instead of this, it is also possible to use esters of diethylaminoethanol with other hydrogen halogenated acids or, for example, with arylsulfonic acids such as toluenesulfonic acid.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH183065T | 1934-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH183065A true CH183065A (en) | 1936-03-15 |
Family
ID=4432003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH183065D CH183065A (en) | 1934-07-12 | 1934-07-12 | Process for the preparation of benzilic acid-2-diethylaminoethanol ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH183065A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2784141A (en) * | 1954-05-13 | 1957-03-05 | Merck & Co Inc | Tranquilizing composition comprising alkyl aminoethyl esters of benzilic acid and salts thereof |
| DE1044102B (en) * | 1953-07-08 | 1958-11-20 | Christian Brunnengraeber Chem | Process for the preparation of esters of xanthene-9-carboxylic acid |
-
1934
- 1934-07-12 CH CH183065D patent/CH183065A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1044102B (en) * | 1953-07-08 | 1958-11-20 | Christian Brunnengraeber Chem | Process for the preparation of esters of xanthene-9-carboxylic acid |
| US2784141A (en) * | 1954-05-13 | 1957-03-05 | Merck & Co Inc | Tranquilizing composition comprising alkyl aminoethyl esters of benzilic acid and salts thereof |
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