DE925717C - Process for the preparation of a basic dibenzofuran derivative and its salts - Google Patents

Process for the preparation of a basic dibenzofuran derivative and its salts

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Publication number
DE925717C
DE925717C DEH16313A DEH0016313A DE925717C DE 925717 C DE925717 C DE 925717C DE H16313 A DEH16313 A DE H16313A DE H0016313 A DEH0016313 A DE H0016313A DE 925717 C DE925717 C DE 925717C
Authority
DE
Germany
Prior art keywords
salts
basic
preparation
acid
dibenzofuran derivative
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEH16313A
Other languages
German (de)
Inventor
Wilhelm Dr Wenner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Application granted granted Critical
Publication of DE925717C publication Critical patent/DE925717C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Verfahren zur Herstellung eines basischen D@ibenzofuranderivates und dessen Salzen Es wurde gefunden, daß 3-Cyclohexyl-aminomethyl-dibenzofuran und seine Salze überraschende chemotherapeutische Eigenschaften, insbesondere in der Bekämpfung von Pilzinfektionen, aufweisen.Process for the preparation of a basic D @ ibenzofuran derivative and its salts It has been found that 3-cyclohexyl-aminomethyl-dibenzofuran and its Salts have surprising chemotherapeutic properties, especially in combating of fungal infections.

Erfindungsgemäß werden die obengenannten Verbindungen der allgemeinen Formel dadurch gewonnen, daß man ein 3-Halogenmethyldibenzofuran, zweckmäßig 3-Chlormethyl-dibenzofuran, mit Cyclohexylamin umsetzt, worauf die erhaltene Base gegebenenfalls mit Säuren zur Bildung der entsprechenden Salze behandelt wird.According to the invention, the abovementioned compounds of the general formula obtained by reacting a 3-halomethyldibenzofuran, expediently 3-chloromethyldibenzofuran, with cyclohexylamine, whereupon the base obtained is optionally treated with acids to form the corresponding salts.

Die Ausgangsverbindungen können in äquimolekularen Mengen zur Reaktion gebracht werden. Es ist jedoch vorteilhaft, mindestens a Mol Cyclohexylamin pro Mol 3-Halogenmethyldibenzofuran zu verwenden, damit das zweite Mol der Stickstoffbase die sich während der Reaktion bildende Halogenwasserstoffsäure neutralisiert. Die Umsetzung erfolgt mit Vorteil in einem organischen Lösungsmittel, beispielsweise Äther, Äthanol, Benzol, Toluol oder Dioxan.The starting compounds can be used in equimolecular amounts for the reaction to be brought. However, it is advantageous to use at least a mole of cyclohexylamine per Use moles of 3-halomethyldibenzofuran, hence the second mole of nitrogen base neutralizes the hydrohalic acid which forms during the reaction. the The reaction is advantageously carried out in an organic solvent, for example Ether, ethanol, benzene, toluene or dioxane.

Die erhaltene Base ist in den üblichen organischen Lösungsmitteln leicht löslich, dagegen in Wasser praktisch unlöslich. Sie bildet leicht Salze mit. anorganischen und organischen Säuren, z. B. mit Salzsäure, Bromwasserstoffsäure, Schwefelsäure, Phosphorsäure, Essigsäure, Benzoesäure, Weinsäure, Oxa säure, Zitronensäure oder Salicylsäure.The base obtained is in the usual organic solvents Easily soluble, but in water practically insoluble. She educates easily salts with. inorganic and organic acids, e.g. B. with hydrochloric acid, hydrobromic acid, Sulfuric acid, phosphoric acid, acetic acid, benzoic acid, tartaric acid, oxa acid, citric acid or salicylic acid.

Die fungicide Wirkung von 3-Cyclohexyl-amino= methyldibenzofüran in vitro an Trychophyton mentagrophytes ist etwa 5omal größer als diejenige von 3-(a-Diäthyl-amino)-äthyl-dibenzofuran.The fungicidal effect of 3-cyclohexyl-amino = methyldibenzofüran in In vitro on Trychophyton mentagrophytes is about 50 times larger than that of 3- (a-diethyl-amino) -ethyl-dibenzofuran.

Beispiel 1o g 3-Chlormethyl-dibenzofuran werden in ioo ccm Toluol gelöst. Man setzt sodann ii g Cyclohexylamin hinzu und erwärmt die Mischung während 3 Stunden auf dem Wasserbad. Man zltriert vom gebildeten Cyclohexylamin-hydrochlorid ab. Das Filtrat wird mit Wasser gewaschen und dann mittels 3o/oiger Salzsäure extrahiert. Aus dem sauren Extrakt scheidet sich ein C51 ab, das bald kristallisiert. Die Kristalle werden durch Umkristallisation aus Wasser gereinigt. Man erhält so 3-Cyclohexyl-aminomethyl-dibenzofuran-hydro-.chlorid vom Schmelzpunkt 2q.8'.Example 10 g of 3-chloromethyl-dibenzofuran are dissolved in 100 cc of toluene solved. One then adds ii g of cyclohexylamine and the mixture is heated during 3 hours on the water bath. The cyclohexylamine hydrochloride formed is filtered off away. The filtrate is washed with water and then extracted with 3% hydrochloric acid. A C51 separates out of the acidic extract and soon crystallizes. The crystals are purified by recrystallization from water. 3-Cyclohexyl-aminomethyl-dibenzofuran-hydrochloride is obtained in this way of melting point 2q.8 '.

Claims (2)

PATENTANSPRÜCHE: i. Verfahren zur Herstellung eines basischen Dibenzofuranderivates und dessen Salzen, dadurch gekennzeichnet, daß ein 3-Halogenmethyldibenzofuran mit Cyclohexylamin umgesetzt und die gewonnene Base gegebenenfalls mit einer Säure behandelt wird. PATENT CLAIMS: i. Process for the preparation of a basic dibenzofuran derivative and its salts, characterized in that a 3-halomethyldibenzofuran with Cyclohexylamine reacted and the base obtained optionally treated with an acid will. 2. Verfahren nach Anspruch i, dadurch gekennzeichnet, daß 2 Mol Cyclohexylamin pro Mol 3-Halogenmethyldibenzofuran verwendet werden. '2. The method according to claim i, characterized in that 2 moles of cyclohexylamine can be used per mole of 3-halomethyldibenzofuran. '
DEH16313A 1951-11-23 1952-09-26 Process for the preparation of a basic dibenzofuran derivative and its salts Expired DE925717C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US925717XA 1951-11-23 1951-11-23

Publications (1)

Publication Number Publication Date
DE925717C true DE925717C (en) 1955-03-28

Family

ID=22233909

Family Applications (1)

Application Number Title Priority Date Filing Date
DEH16313A Expired DE925717C (en) 1951-11-23 1952-09-26 Process for the preparation of a basic dibenzofuran derivative and its salts

Country Status (1)

Country Link
DE (1) DE925717C (en)

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