CH304888A - Process for the preparation of a new furan compound. - Google Patents

Process for the preparation of a new furan compound.

Info

Publication number
CH304888A
CH304888A CH304888DA CH304888A CH 304888 A CH304888 A CH 304888A CH 304888D A CH304888D A CH 304888DA CH 304888 A CH304888 A CH 304888A
Authority
CH
Switzerland
Prior art keywords
preparation
furan compound
act
phenyl
ethyl
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH304888A publication Critical patent/CH304888A/en

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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
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Verfahren        zur    Herstellung einer neuen     Furanverbindung.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur     Herstellung    des im Schweiz.  Patent Nr.

   300195 beschriebenen     2-(N-Phenyl-          äthyl-methylaminomethyl)    -     tetrahydrofurans,     welches dadurch gekennzeichnet ist, dass man  auf     N-(ss-Phenyl-äthyl)-methylamin    eine Ver  bindung der     Formel     
EMI0001.0010     
    worin X einen bei der Reaktion sich abspal  tenden Rest bedeutet, insbesondere einen re  aktionsfähigen Ester des     Tetrahydrofuryl-(2)-          methylalkohols,    z. B. mit einer starken anor  ganischen oder organischen Säure einwirken  lässt.  



  Die Reaktion wird zweckmässig     in    Gegen  wart eines     säurebindenden    Mittels, wie     Ka-          liumcarbonat,        und    vorzugsweise bei erhöhter  Temperatur     durchgeführt.     



  Die Base kann in üblicher Weise in ihre       Salze        übergeführt    werden, so zum Beispiel in  das Hydrochlorid vom F.126-128 .  



  <B>A</B>  <I>Beispiel:</I>  27 Gewichtsteile     N-Phenyläthyl-methyl-          amin,    41,2 Gewichtsteile     Tetrahydrofuryl-(2)-          methylbromid    und 35 Gewichtsteile     Kalium-          bicarbonat    werden unter Rühren während  2 Stunden auf 120  erhitzt. Nach dem Kühlen  wird das Gemisch mit     verdünnter    Schwefel  säure sauer gestellt und mit Äther extrahiert.

      Die verbleibende wässerige Phase wird hier  auf mit Natronlauge     alkalisiert    und die abge  schiedene Base in Äther     aufgenommen.    Nach  dem Trocknen und     Verdampfen.    des Äthers  erhält man durch Destillation das     2-(N-Phe-          nyläthyl-methylaminomethyl)-tetrahydrofuran     der Formel  
EMI0001.0033     
    vom     Kp.110-112     bei 0,05 mm     Hg.    Sein     Hy-          drochlorid    schmilzt bei 126-128 .



      Process for the preparation of a new furan compound. The subject of the present patent is a process for the production of in Switzerland. Patent no.

   300195 described 2- (N-phenyl-ethyl-methylaminomethyl) - tetrahydrofuran, which is characterized in that there is a compound of the formula on N- (s-phenyl-ethyl) -methylamine
EMI0001.0010
    wherein X is a residue that splits off in the reaction, in particular a re active ester of tetrahydrofuryl (2) - methyl alcohol, for. B. can act with a strong inorganic or organic acid.



  The reaction is expediently carried out in the presence of an acid-binding agent such as potassium carbonate, and preferably at an elevated temperature.



  The base can be converted into its salts in the usual way, for example into the hydrochloride from F.126-128.



  <B> A </B> <I> Example: </I> 27 parts by weight of N-phenylethyl-methylamine, 41.2 parts by weight of tetrahydrofuryl- (2) -methyl bromide and 35 parts by weight of potassium bicarbonate are stirred for 2 hours heated to 120. After cooling, the mixture is acidified with dilute sulfuric acid and extracted with ether.

      The remaining aqueous phase is made alkaline with sodium hydroxide solution and the separated base is taken up in ether. After drying and evaporation. of the ether, 2- (N-phenylethyl-methylaminomethyl) -tetrahydrofuran of the formula is obtained by distillation
EMI0001.0033
    of bp 110-112 at 0.05 mm Hg. Its hydrochloride melts at 126-128.

Claims (1)

PATENTANSPRUCH: Verfahren zur'Herstellung des im Schweiz. Patent Nr. 300195 beschriebenen 2-(N-Phenyl- äthyl-methylaminomethyl)-tetrahydrofurans, dadurch gekennzeichnet, dass man auf N-(8- Phenyl:-äthyl)-methylamin eine Verbindung der Formel EMI0001.0044 worin X einen bei der Reaktion sich abspal tenden Rest bedeutet, einwirken lässt. UNTERANSPRÜCHE: 1. PATENT CLAIM: Process for the production of the in Switzerland. Patent No. 300195 described 2- (N-phenyl-ethyl-methylaminomethyl) -tetrahydrofuran, characterized in that on N- (8-phenyl: -ethyl) -methylamine, a compound of the formula EMI0001.0044 where X is a residue that splits off during the reaction, can act. SUBCLAIMS: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man einen reak- tionsfähigen Ester des Tetrahydrofuryl-(2)- methylalkohols einwirken lässt. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man Tetrahydroftiryl-(2)-methylbromid' einwirken l asst. Process according to patent claim, characterized in that a reactive ester of tetrahydrofuryl (2) methyl alcohol is allowed to act. 2. The method according to claim and dependent claim 1, characterized in that tetrahydroftiryl- (2) -methylbromide 'is allowed to act. 3, Verfahren nach Patentanspruch und .den Unteransprüchen 1 und 2, dadurch ge kennzeichnet, dass man die Reaktion in Gegen wart eines säurebindenden Mittels durchführt. 3, the method according to patent claim and .den claims 1 and 2, characterized in that the reaction is carried out in the presence of an acid-binding agent.
CH304888D 1951-03-22 1951-03-22 Process for the preparation of a new furan compound. CH304888A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH304888T 1951-03-22

Publications (1)

Publication Number Publication Date
CH304888A true CH304888A (en) 1955-01-31

Family

ID=4492258

Family Applications (1)

Application Number Title Priority Date Filing Date
CH304888D CH304888A (en) 1951-03-22 1951-03-22 Process for the preparation of a new furan compound.

Country Status (1)

Country Link
CH (1) CH304888A (en)

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