CH258207A - Process for the preparation of an araliphatic amine. - Google Patents

Process for the preparation of an araliphatic amine.

Info

Publication number
CH258207A
CH258207A CH258207DA CH258207A CH 258207 A CH258207 A CH 258207A CH 258207D A CH258207D A CH 258207DA CH 258207 A CH258207 A CH 258207A
Authority
CH
Switzerland
Prior art keywords
preparation
methyl
methoxyphenoxy
phenyl
araliphatic amine
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R 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 Ag J R Geigy filed Critical Ag J R Geigy
Publication of CH258207A publication Critical patent/CH258207A/en

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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
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring

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

Description

  

  Verfahren zur Herstellung eines     araliphatischen    Amins.    Gegenstand vorliegenden Patentes ist ein  Verfahren zur     Herstellung    eines     araliphati-          schen    Amins.

   Das, Verfahren ist. dadurch ge  kennzeichnet,     da.ss    man 1-     [4'-(4"-Methoxy-          phenoxy)-phenyl]        -2-methy        l-pentanon-(3)-    mit       3Tethylforma.mid.erhitzt    und die     entstandene          Formylaminoverbindung        hydrolysiert.    Die  neue Verbindung, das     1-[4'-(4"-Methoxy-          phenoxy)    -     phenyl]        -2-methyil-3-methyl-amino-          penta.n,    siedet unter 0,5 mm Druck bei 172 .

    Sie soll als     Arzneimittel    Verwendung finden.    <I>Beispiel:</I>  20 Teile     1-[4'-(4"-Methoxy-phenoxy)-phe-          nyl]-2-methyl-pentanon-(3)    werden     mit    31,4  Teilen     Methylformamid    während acht Stun  den auf 165 bis 170  erhitzt.

   Nach dem Ab  kühlen     hydrol'ysiert    man die entstandene       Formylverbindung    durch dreistündiges Er  hitzen, am     Rückfluss    mit 100 Teilen konzen  trierter     Salzsäure.    Nach dem Erkalten ver  dünnt man mit     Wasser,    macht mit     konzen-          trierter    Natronlauge alkalisch und nimmt die    abgeschiedene Base in Äther auf.

   Nach dem       Verjagen,    des     Lösungsmittels    wird der Rück  stand in verdünnter Salzsäure     aufgenommen,     diese Lösung     ausgeäthert,    die Base mit     Na-          tronIlauge    wieder frei gemacht, in Äther auf  genommen und die ätherische Lösung mit       wasserfreiem        Natriumsulfat    getrocknet. Der  Äther wird anschliessend     abdestilliert    und die  Base fraktioniert.

   Das     1-[4'-(4"-Methoxy-          phenoxy)        -phenyl]A        -methyl-3-methylamino-          pentan        destilliert    bei 172      und    0,5     mm.  



  Process for the preparation of an araliphatic amine. The present patent relates to a process for the preparation of an araliphatic amine.

   That, procedure is. characterized in that 1- [4 '- (4 "-methoxyphenoxy) -phenyl] -2-methyl-pentanone- (3) - is heated with 3Tethylforma.mid.erhitzt and the resulting formylamino compound hydrolyzed New compound, the 1- [4 '- (4 "-Methoxyphenoxy) - phenyl] -2-methyl-3-methyl-aminopenta.n, boils under 0.5 mm pressure at 172.

    It should be used as a medicine. <I> Example: </I> 20 parts of 1- [4 '- (4 "-methoxyphenoxy) -phenyl] -2-methyl-pentanone- (3) are mixed with 31.4 parts of methylformamide for eight hours heated to 165-170.

   After cooling, the formyl compound formed is hydrolyzed by heating for three hours under reflux with 100 parts of concentrated hydrochloric acid. After cooling, it is thinned with water, made alkaline with concentrated sodium hydroxide solution, and the separated base is taken up in ether.

   After chasing away the solvent, the residue is taken up in dilute hydrochloric acid, this solution is extracted with ether, the base is freed again with sodium hydroxide solution, taken up in ether and the ethereal solution is dried with anhydrous sodium sulfate. The ether is then distilled off and the base is fractionated.

   The 1- [4 '- (4 "-methoxyphenoxy) -phenyl] A -methyl-3-methylaminopentane distills at 172 and 0.5 mm.

Claims (1)

PATENTANSPRUCH: Verfahren. zur Herstellung eines 9,ra!lipha- tischen Amins, dadurch gekennzeichnet, dass man 1-[4'-(4"-Methoxy-phenoxy)-phenyl]-2- methyl-pentanon-(3) mit Methylformamid erhitzt und die entstandene Formylaminover- bindung hydrolysiert. Die neue Verbindung, das 1-[4'-(4"-Methoxy-phenoxy)-phenyl]-2- methyl-3-methylamino-pentan, siedet unter 0.5 mm Druck bei 172 . PATENT CLAIM: Process. for the preparation of a 9, ra! lipha- tischen amine, characterized in that 1- [4 '- (4 "-Methoxyphenoxy) -phenyl] -2-methyl-pentanone- (3) is heated with methylformamide and the resulting The new compound, 1- [4 '- (4 "-methoxyphenoxy) -phenyl] -2-methyl-3-methylamino-pentane, boils under 0.5 mm pressure at 172.
CH258207D 1945-05-08 1945-05-08 Process for the preparation of an araliphatic amine. CH258207A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH252237T 1945-05-08
CH258207T 1945-05-08

Publications (1)

Publication Number Publication Date
CH258207A true CH258207A (en) 1948-11-15

Family

ID=25729602

Family Applications (1)

Application Number Title Priority Date Filing Date
CH258207D CH258207A (en) 1945-05-08 1945-05-08 Process for the preparation of an araliphatic amine.

Country Status (1)

Country Link
CH (1) CH258207A (en)

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