CH240143A - Process for the preparation of a basic aralkyl ether. - Google Patents
Process for the preparation of a basic aralkyl ether.Info
- Publication number
- CH240143A CH240143A CH240143DA CH240143A CH 240143 A CH240143 A CH 240143A CH 240143D A CH240143D A CH 240143DA CH 240143 A CH240143 A CH 240143A
- Authority
- CH
- Switzerland
- Prior art keywords
- basic
- ether
- preparation
- aralkyl ether
- parts
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
- C07C217/10—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Darstellung eines basischen Aralkyläthers. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines basischen Aralkyläthers aus Cyclohegyl-(o- methoxy-phenyl)-carbinol und Diäthylamino- äthanol. Das Verfahren ist dadurch gekenn zeichnet, dass ein reaktionsfähiger Ester des einen Alkohols mit einem Alkoholat des andern. Alkohols umgesetzt wird.
Der erhal tene Cyclo#hexyl - (o-methogy-phenyl) - carbin- (diäthylaminoäthyl)-äther ist eine Flüssigkeit vom Kp. a,, 161-163 ; er soll therapeutische Verwendung finden.
<I>Beispiel:</I> Zu einer Suspension von 4 Teilen pulveri siertem Natriumamid in 200 Teilen absolu tem Benzol werden 22 Teile Cyclohexyl- (o-methoxy-phenyl)-carbinol zugetropft und eine Stunde bei 60 gerührt. Dann werden 14 Teile ss-Chloräthyl-diäthylamin zugegeben und das Ganze sechs Stunden unter Rückfluss und Rühren erhitzt. Nach dem Abkühlen wird mit. Wasser versetzt und mit 10%iger Salz säure mehrmals ausgeschüttelt.
Die vereinig- ten sälzsauren Auszüge werden mit Pottasche alkalisch gemacht, die ausgeschiedene Base in Äther aufgenommen, die Atherlösung mit konzentrierter Pottaschelösung gewaschen, über fester Pottasche getrocknet und der Äther abgedampft. Der Rückstand siedet unter 0,9 mm bei 161-163 .
Dieselbe Verbindung kann auch auf fol gende Weise erhalten werden: In einer Lö sung von 11 Teilen Diäthylaminoäthanol in 40 Teilen Benzol werden 2 Teile Natrium auf gelöst. Nach .dem Erkalten wird die berech nete Menge Cyclohexyl-(o-methoxy-phenyl)- carbinyl-chlorid in Portionen zugegeben. Nach Abklingen der Reaktion wird noch eine Stunde lang am Rückflusskühler auf dem Wasserbad erhitzt, alsdann gekühlt, mit Wasser aus geschüttelt und schliesslich unter Kühlung mit verdünnter Salzsäure verrührt.
Nach noch maligem Waschen des Benzols mit Wasser werden die vereinigten Auszüge mit Pottasche gefällt und die ausgeschiedene Base in Äther aufgenommen. Nach Entfernen des Lösungs mittels destilliert die Base bei l61-163 und 0,9 mm. Der neue Äther soll therapeutische Verwendung finden.
Process for the preparation of a basic aralkyl ether. The subject of the present Zusatzpaten tes is a method for the preparation of a basic aralkyl ether from cyclohegyl- (o-methoxy-phenyl) -carbinol and diethylamino-ethanol. The method is characterized in that a reactive ester of one alcohol with an alcoholate of the other. Alcohol is implemented.
The obtained cyclo # hexyl - (o-methogy-phenyl) -carbine- (diethylaminoethyl) -ether is a liquid of Kp. A ,, 161-163; it should find therapeutic use.
<I> Example: </I> 22 parts of cyclohexyl (o-methoxyphenyl) carbinol are added dropwise to a suspension of 4 parts of powdered sodium amide in 200 parts of absolute benzene, and the mixture is stirred at 60 for one hour. 14 parts of ß-chloroethyl-diethylamine are then added and the whole is heated under reflux and stirring for six hours. After cooling down, use. Added water and extracted several times with 10% hydrochloric acid.
The combined hydrochloric acid extracts are made alkaline with potash, the base which has separated out is taken up in ether, the ether solution is washed with concentrated potash solution, dried over solid potash and the ether is evaporated. The residue boils below 0.9 mm at 161-163.
The same compound can also be obtained in the following manner: 2 parts of sodium are dissolved in a solution of 11 parts of diethylaminoethanol in 40 parts of benzene. After cooling down, the calculated amount of cyclohexyl (o-methoxyphenyl) carbinyl chloride is added in portions. After the reaction has subsided, the mixture is heated in the reflux condenser on the water bath for a further hour, then cooled, shaken out with water and finally stirred with dilute hydrochloric acid while cooling.
After washing the benzene again with water, the combined extracts are precipitated with potash and the base which has separated out is taken up in ether. After removing the solution by means of the base distilled at 161-163 and 0.9 mm. The new ether should be used therapeutically.
Claims (1)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH2397799X | 1942-09-23 | ||
CH240143T | 1942-09-23 | ||
GB15558/43A GB585994A (en) | 1943-09-22 | 1943-09-22 | Manufacture of aminoalkyl ethers and of quaternary ammonium compounds formed therefrom |
Publications (1)
Publication Number | Publication Date |
---|---|
CH240143A true CH240143A (en) | 1945-11-30 |
Family
ID=32110427
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH240143D CH240143A (en) | 1942-09-23 | 1942-09-23 | Process for the preparation of a basic aralkyl ether. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH240143A (en) |
-
1942
- 1942-09-23 CH CH240143D patent/CH240143A/en unknown
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