CH149007A - Process for the preparation of a halogen-containing basic ether. - Google Patents

Process for the preparation of a halogen-containing basic ether.

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Publication number
CH149007A
CH149007A CH149007DA CH149007A CH 149007 A CH149007 A CH 149007A CH 149007D A CH149007D A CH 149007DA CH 149007 A CH149007 A CH 149007A
Authority
CH
Switzerland
Prior art keywords
halogen
preparation
dibromo
basic ether
containing basic
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH149007A publication Critical patent/CH149007A/en

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Description

  

  Verfahren zur Darstellung eines     halogenhaltigen    basischen Äthers.    Es wurde gefunden, dass man zu einem  halogenhaltigen, basischen Äther gelangen  kann, wenn man     einen    reaktionsfähigen Ester  des     Diäthylaminoäthanols'    in     Gegenwart     säurebindender Mittel auf     1,6-Dibrom-2-          na.phtol    einwirken lässt.  



  Das     1,6-Dibrom-2-diäthylaminoäthoxy-          naphtalin    bildet ein farbloses Kristallpulver  vom Schmelzpunkt 65 bis 66  . Das farblose       Hydrochlorid    schmilzt bei 164 bis 165  .  Es ist leicht löslich in Wasser.  



  Die neue Verbindung soll zu therapeu  tischen Zwecken Verwendung finden.  <I>Beispiel:</I>  1,6 Teile     1,6-Dibrom-2-naphtol,    1     Teil          Chloräthy        ldiäthylaminhydrochlorid    und 2,2  Teile Pottasche werden in Aceton unter Rüh  ren     gekocht.    Nach beendigter Reaktion     wird     vom anorganischen     Anteil        abgenutscht    und  das Aceton     abdestilliert.    Der Rückstand     wird     in Äther aufgenommen und die Lösung mehr-         mals    mit verdünnter Natronlauge behandelt.

    Nach dem Vertreiben des Lösungsmittels  bleibt das     1,6-Dibrom-2-diäthylaminoäthoxy-          naphtalin    als farbloses Kristallpulver zu  rück.  



  Die Reaktion kann auch in andern  Lösungsmitteln, zum Beispiel in Alkohol  oder Wasser,     ausgeführt    werden. Als säure  bindende Mittel kommen ferner andere al  kalisch reagierende Verbindungen, wie zum  Beispiel die     Hydroxyde    oder     Alkoholate    der  Alkali- oder     Erdalkälimetalle,    in Betracht.  Ausserdem kann man an Stelle von Halogen  äthyldiätbylamin auch andere reaktions  fähige Ester des     Diäthylaminoäthanols,    zum  Beispiel diejenigen aromatischer     Sulfosäuren,     verwenden.



  Process for the preparation of a halogen-containing basic ether. It has been found that a halogen-containing, basic ether can be obtained if a reactive ester of diethylaminoethanol is allowed to act on 1,6-dibromo-2-na.phtol in the presence of acid-binding agents.



  The 1,6-dibromo-2-diethylaminoethoxynaphthalene forms a colorless crystal powder with a melting point of 65 to 66. The colorless hydrochloride melts at 164 to 165. It is easily soluble in water.



  The new connection is intended to be used for therapeutic purposes. <I> Example: </I> 1.6 parts of 1,6-dibromo-2-naphthol, 1 part of chloroethyl diethylamine hydrochloride and 2.2 parts of potash are boiled in acetone with stirring. After the reaction has ended, the inorganic component is suction filtered and the acetone is distilled off. The residue is taken up in ether and the solution is treated several times with dilute sodium hydroxide solution.

    After the solvent has been driven off, the 1,6-dibromo-2-diethylaminoethoxy naphthalene remains as a colorless crystal powder.



  The reaction can also be carried out in other solvents, for example in alcohol or water. Other alkaline compounds, such as, for example, the hydroxides or alcoholates of the alkali or alkaline earth metals, can also be used as acid-binding agents. In addition, other reactive esters of diethylaminoethanol, for example those of aromatic sulfonic acids, can be used instead of halogen ethyl dietbylamine.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines halogen- haltigen, basischen Äthers, dadurch gekenn zeichnet, dass man einen reaktionsfähigen Ester des Diäthylaminoäthanols in Gegen- wart säurebindender Mittel auf 1,6-Dibrom- 2-naphtol einwirken lässt. Das 1,6-Dibrom-2-diäthylaminoäthoxy- naphtalin bildet ein farbloses Kristallpulver vom Schmelzpunkt 65 bis 66 . Das farblose Hydrochlorid schmilzt bei 164 bis 165 . Es ist leicht löslich in Wasser. PATENT CLAIM: Process for the preparation of a halogen-containing, basic ether, characterized in that a reactive ester of diethylaminoethanol is allowed to act on 1,6-dibromo-2-naphthol in the presence of acid-binding agents. The 1,6-dibromo-2-diethylaminoethoxynaphthalene forms a colorless crystal powder with a melting point of 65 to 66. The colorless hydrochloride melts at 164 to 165. It is easily soluble in water. Die neue Verbindung soll zu therapeu tischen Zwecken Verwendung finden. The new connection is intended to be used for therapeutic purposes.
CH149007D 1929-04-05 1929-04-05 Process for the preparation of a halogen-containing basic ether. CH149007A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH146120T 1929-04-05
CH149007T 1929-04-05

Publications (1)

Publication Number Publication Date
CH149007A true CH149007A (en) 1931-08-15

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ID=25714809

Family Applications (1)

Application Number Title Priority Date Filing Date
CH149007D CH149007A (en) 1929-04-05 1929-04-05 Process for the preparation of a halogen-containing basic ether.

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CH (1) CH149007A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004043458A1 (en) * 2002-11-12 2004-05-27 Abbott Laboratories Bicyclic-substituted amines as histamine-3 receptor ligands
US7098222B2 (en) 2004-05-12 2006-08-29 Abbott Laboratories Bicyclic-substituted amines having cyclic-substituted monocyclic substituents
US7145005B2 (en) 2004-05-12 2006-12-05 Abbott Laboratories 2-(6-{2-[(2R)-2-Methyl-1-pyrrolidin-1-yl]-ethyl}-2-naphthalen-2-yl)-2H-pyridazin-3-one salts and their preparation
US7153889B2 (en) 2002-11-12 2006-12-26 Abbott Laboratories Bicyclic-substituted amines as histamine-3 receptor ligands
US7205316B2 (en) 2004-05-12 2007-04-17 Abbott Laboratories Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004043458A1 (en) * 2002-11-12 2004-05-27 Abbott Laboratories Bicyclic-substituted amines as histamine-3 receptor ligands
JP2006514926A (en) * 2002-11-12 2006-05-18 アボット・ラボラトリーズ Bicyclic substituted amines as histamine-3 receptor ligands
US7153889B2 (en) 2002-11-12 2006-12-26 Abbott Laboratories Bicyclic-substituted amines as histamine-3 receptor ligands
US7456196B2 (en) 2002-11-12 2008-11-25 Abbott Laboratories Bicyclic-substituted amines as histamine-3 receptor ligands
US7947711B2 (en) 2002-11-12 2011-05-24 Abbott Laboratories Bicyclic-substituted amines as histamine-3 receptor ligands
JP4820094B2 (en) * 2002-11-12 2011-11-24 アボット・ラボラトリーズ Bicyclic substituted amines as histamine-3 receptor ligands
US8273767B2 (en) 2002-11-12 2012-09-25 Abbott Laboratories Bicyclic-substituted amines as histamine-3 receptor ligands
US7098222B2 (en) 2004-05-12 2006-08-29 Abbott Laboratories Bicyclic-substituted amines having cyclic-substituted monocyclic substituents
US7145005B2 (en) 2004-05-12 2006-12-05 Abbott Laboratories 2-(6-{2-[(2R)-2-Methyl-1-pyrrolidin-1-yl]-ethyl}-2-naphthalen-2-yl)-2H-pyridazin-3-one salts and their preparation
US7205316B2 (en) 2004-05-12 2007-04-17 Abbott Laboratories Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands

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