CH262486A - Process for the preparation of an araliphatic amine. - Google Patents

Process for the preparation of an araliphatic amine.

Info

Publication number
CH262486A
CH262486A CH262486DA CH262486A CH 262486 A CH262486 A CH 262486A CH 262486D A CH262486D A CH 262486DA CH 262486 A CH262486 A CH 262486A
Authority
CH
Switzerland
Prior art keywords
methyl
preparation
parts
reducing agent
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 CH262486A publication Critical patent/CH262486A/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, dass man     1-(4'-n-Hexyloxy-          phenyl)    - 2 -     methyl    -     pentanon-    (3) mit einem  Reduktionsmittel in Gegenwart von Mono  methylamin behandelt. Die entstandene, neue  Verbindung, das     1-(4'-n-Hexyloxy-phenyl)-2-          methyl-3-metlLylamino-pentan,    siedet unter  0,15 mm Druck bei 1180. Sie soll als Arznei  mittel Verwendung finden.  



       Beispiel   <I>1:</I>  20 Teile     1-(4'-Hexyloxy-phenyl)-2-methyl-          pentanon-(3)        werden        in        110        Teilen     Alkohol gelöst und nach Zusatz von 10 Teilen  wässriger 41     J        iger        Monomethylaminlösung    bei  50 bis     601)    mit 5 Teilen Aluminiumamalgam  versetzt.

   Nach Beendigung der Reduktion  wird vom     Aluminiumhydroxyd        abfiltriert,     dieses gut mit Alkohol gewaschen, der Alko  hol     abdestilliert    und das gebildete sekundäre  Amin in verdünnter Salzsäure gelöst. Diese  Lösung wird mit Äther von den nichtbasischen  Bestandteilen befreit und die Base mit Na  tronlauge in Freiheit gesetzt. Sie wird in  Äther aufgenommen, die Lösung mit wasser  freiem Glaubersalz getrocknet, der Äther ab  destilliert und die freie Base, das 1-(4'-IIexyl-         oxy-phenyl)    - 2 -     methyl-3-methylamino-pentan,     bei 1180 und 0,15 mm im Vakuum destilliert.

    <I>Beispiel 2:</I>  27 Teile     1-(4'-Hexyloxy-phenyl)-2-methyl-          pentanon-    (3) und 6 Teile     Methylamin    wur  den in 60 Teilen absolutem Alkohol gelöst  und bei 500 mit 0,5 Teilen Platinoxyd hy  driert, bis die berechnete Menge Wasserstoff  aufgenommen worden ist. Nach dem Filtrie  ren wird die Base nach Beispiel 1 isoliert und  destilliert.



  Process for the preparation of an araliphatic amine. The present patent relates to a process for the preparation of an araliphatic amine. The process is characterized in that 1- (4'-n-hexyloxyphenyl) -2-methyl-pentanone- (3) is treated with a reducing agent in the presence of monomethylamine. The resulting new compound, 1- (4'-n-hexyloxyphenyl) -2-methyl-3-methylamino-pentane, boils under 0.15 mm pressure at 1180. It is said to be used as a medicament.



       Example <I> 1: </I> 20 parts of 1- (4'-hexyloxyphenyl) -2-methyl-pentanone- (3) are dissolved in 110 parts of alcohol and, after addition of 10 parts of aqueous 41% monomethylamine solution, are added 50 to 601) mixed with 5 parts of aluminum amalgam.

   After the reduction is complete, the aluminum hydroxide is filtered off, washed thoroughly with alcohol, the alcohol is distilled off and the secondary amine formed is dissolved in dilute hydrochloric acid. This solution is freed from the non-basic components with ether and the base is set free with sodium hydroxide solution. It is taken up in ether, the solution is dried with anhydrous Glauber's salt, the ether is distilled off and the free base, 1- (4'-IIexyl-oxy-phenyl) -2-methyl-3-methylamino-pentane, at 1180 and 0.15 mm distilled in vacuo.

    <I> Example 2: </I> 27 parts of 1- (4'-hexyloxyphenyl) -2-methyl-pentanone- (3) and 6 parts of methylamine WUR dissolved in 60 parts of absolute alcohol and at 500 with 0, 5 parts of platinum oxide hydrogenated until the calculated amount of hydrogen has been absorbed. After Filtrie ren, the base is isolated according to Example 1 and distilled.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines aralipha- tischen Amins, dadurch gekennzeichnet, dass man 1-(4'-n - IIexyloxy - phenyl)-2-methyl- pentanon-(3) mit einem Reduktionsmittel in Gegenwart von Monomethylamin behandelt. Die entstandene, neue Verbindung, das 1-(4'- n-Ilexyloxy-phenyl) - 2-methyl-3-methylamino- pentan, siedet unter 0,15 mm Druck bei 1180. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch., da durch gekennzeichnet, dass als Reduktionsmit tel amalgamiertes Aluminium verwendet wird. 2. Claim: Process for the production of an araliphatic amine, characterized in that 1- (4'-n-IIexyloxy-phenyl) -2-methyl-pentanone- (3) is treated with a reducing agent in the presence of monomethylamine. The resulting, new compound, 1- (4'-n-Ilexyloxy-phenyl) -2-methyl-3-methylamino-pentane, boils under 0.15 mm pressure at 1180. SUBClaims: 1. Method according to patent claim., Da characterized in that amalgamated aluminum is used as the reducing agent. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass als Reduktionsmit tel katalytisch erregter Wasserstoff verwen det wird. Method according to claim, characterized in that catalytically excited hydrogen is used as the reducing agent.
CH262486D 1948-02-11 1948-02-11 Process for the preparation of an araliphatic amine. CH262486A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH245838T 1948-02-11
CH262486T 1948-02-11

Publications (1)

Publication Number Publication Date
CH262486A true CH262486A (en) 1949-06-30

Family

ID=25729077

Family Applications (1)

Application Number Title Priority Date Filing Date
CH262486D CH262486A (en) 1948-02-11 1948-02-11 Process for the preparation of an araliphatic amine.

Country Status (1)

Country Link
CH (1) CH262486A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0339878A2 (en) * 1988-04-25 1989-11-02 Eli Lilly And Company Propanamine derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0339878A2 (en) * 1988-04-25 1989-11-02 Eli Lilly And Company Propanamine derivatives
EP0339878A3 (en) * 1988-04-25 1990-12-05 Eli Lilly And Company Propanamine derivatives

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