CH116035A - Process for the preparation of 1-methyl-4-diethylaminoethyl ether of hydroquinone. - Google Patents

Process for the preparation of 1-methyl-4-diethylaminoethyl ether of hydroquinone.

Info

Publication number
CH116035A
CH116035A CH116035DA CH116035A CH 116035 A CH116035 A CH 116035A CH 116035D A CH116035D A CH 116035DA CH 116035 A CH116035 A CH 116035A
Authority
CH
Switzerland
Prior art keywords
hydroquinone
methyl
preparation
ether
diethylaminoethyl ether
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH116035A publication Critical patent/CH116035A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  Verfahren zur Darstellung des     1-1VIethyl-4-diäthylaminoäthyläthers    des     Hydrochinons.       Es wurde gefunden, dass der     1-Methyl-4-          diäthylaminoäthyläther    des     Hydrochinons     ausgesprochene physiologische Eigenschaften  zeigt. Der neue Körper hat sich besonders  wirksam     erwiesen    bei     Erkrankungen    des  Herzens. Er wirkt blutdruckherabsetzend,  verlangsamt den Puls und     übertrifft    in die  ser Hinsicht die analogen     ortho-    oder     meta-          substituierten.    Verbindungen.

   Man kann ihn  in glatter Reaktion mit vorzüglicher Aus  beute in der Weise darstellen, dass man in  Gegenwart alkalisch wirkender Mittel auf       Hydrochinonmonomethyläther        Diäthylamino-          Chloräthanol    einwirken lässt.  



       Beispiel:     3,7     Gewichtsteile    Natrium werden in 50  Gewichtsteilen Alkohol aufgelöst und mit  20 Gewichtsteilen     Hydrochinonmonomeiihyl-          äther    und 25 Gewichtsteilen     Diäthylamino-          chloräthanol    versetzt. Die Reaktion beginnt  schon bei Zimmertemperatur und wird durch  Erwärmen vervollständigt. Dann wird in  Wasser gegossen, das sich abscheidende Öl  abgehoben, getrocknet und destilliert.

      Bei 15 mm Druck geht der     1-Methyl-4-          diäthylaminoäthylhydrochinonäther     
EMI0001.0023     
    als farblose Flüssigkeit über, die mit Säuren  nach den üblichen Methoden erhältliche gut  kristallisierende Salze bildet. Das     salzsaure     Salz zum Beispiel kristallisiert aus Essig  ester in farblosen Nadeln, die bei 121 bis  122   schmelzen.



  Process for the preparation of 1-1VIethyl-4-diethylaminoäthyläthers of hydroquinone. It has been found that the 1-methyl-4-diethylaminoethyl ether of hydroquinone shows pronounced physiological properties. The new body has proven to be particularly effective in treating heart diseases. It has a blood pressure lowering effect, slows down the pulse and in this respect surpasses the analogous ortho- or meta-substituted ones. Links.

   You can show it in a smooth reaction with excellent booty in such a way that you can act in the presence of alkaline agents on hydroquinone monomethyl ether diethylamino-chloroethanol.



       Example: 3.7 parts by weight of sodium are dissolved in 50 parts by weight of alcohol, and 20 parts by weight of hydroquinone monomethyl ether and 25 parts by weight of diethylamino chloroethanol are added. The reaction begins at room temperature and is completed by heating. Then it is poured into water, the oil that separates is lifted off, dried and distilled.

      The 1-methyl-4-diethylaminoethylhydroquinone ether is released at 15 mm pressure
EMI0001.0023
    as a colorless liquid which forms readily crystallizing salts with acids which can be obtained by conventional methods. The hydrochloric acid salt, for example, crystallizes from ethyl acetate in colorless needles that melt at 121 to 122.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung des 1-Methyl- 4-diäthylaminoäthyläthers des Hydrochinons, dadurch gekennzeichnet, dass man in Gegen wart von alkalisch wirkenden Mitteln auf Hydrochinonmonomethyläther Diäthylamino- chloräthanol einwirken lässt. Der neue-Kör- per geht, im Vakuum destilliert, als farb lose Flüssigkeit über; er bildet mit Säuren gut kristallisierte Salze. Sein salzsaure Salz kristallisiert aus Essigester in farblosen Nadeln, die bei 121 bis 122 schmelzen. PATENT CLAIM: Process for the preparation of 1-methyl-4-diethylaminoethyl ether of hydroquinone, characterized in that diethylamino-chloroethanol is allowed to act on hydroquinone monomethyl ether in the presence of alkaline agents. The new body, distilled in vacuo, passes over as a colorless liquid; it forms well-crystallized salts with acids. Its hydrochloric acid salt crystallizes from ethyl acetate in colorless needles that melt at 121 to 122. Das neue Produkt hat sich als besonders wirksam bei Erkrankungen des Herzens er wiesen. Es wirkt blutdruckherabsetzend, --erlang samt den Puls und übertrifft in die ser Hinsicht die analogen ortho- oder meta- substituierten Verbindungen. The new product has proven to be particularly effective in treating heart diseases. It has a blood pressure lowering effect, slows down including the pulse and in this respect surpasses the analogous ortho- or meta-substituted compounds.
CH116035D 1925-02-11 1925-02-11 Process for the preparation of 1-methyl-4-diethylaminoethyl ether of hydroquinone. CH116035A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH116035T 1925-02-11

Publications (1)

Publication Number Publication Date
CH116035A true CH116035A (en) 1926-08-02

Family

ID=4375072

Family Applications (1)

Application Number Title Priority Date Filing Date
CH116035D CH116035A (en) 1925-02-11 1925-02-11 Process for the preparation of 1-methyl-4-diethylaminoethyl ether of hydroquinone.

Country Status (1)

Country Link
CH (1) CH116035A (en)

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