CH252238A - Process for the preparation of an araliphatic amine. - Google Patents

Process for the preparation of an araliphatic amine.

Info

Publication number
CH252238A
CH252238A CH252238DA CH252238A CH 252238 A CH252238 A CH 252238A CH 252238D A CH252238D A CH 252238DA CH 252238 A CH252238 A CH 252238A
Authority
CH
Switzerland
Prior art keywords
preparation
methyl
amine
araliphatic amine
araliphatic
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 CH252238A publication Critical patent/CH252238A/en

Links

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

Landscapes

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

Description

  

  Verfahren zur Herstellung     eines        araliphatisehen        Amins.       Gegenstand vorliegenden Patentes äst ein  Verfahren zur     Herstellung    eines     araliphati-          schen        Amins.    Das Verfahren ist dadurch ge  kennzeichnet, dass man     1-(3'-Halogen-4'-me-          thoxy-phenyl)-2-methyl-pentanon-(3)    in Ge  genwart von     Monomethyl-amin        mit    einem Re  duktionsmittel behandelt,

   wobei unter gleich  zeitigem Ersatz des Halogens durch     Wasser-          stoff    das     3-Methylamino-Derivat    des Aus  gangsstoffes gebildet wird.     Die,    entstandene  neue Verbindung, das     1-(4'-1YIethoxy-phenyl)-          2-methyl-3-methylamino-pentan,    siedet unter  0,5 mm Druck     bei    102 . Sie soll     als    Arznei  mittel Verwendung finden.  



       Beispiel:     20 Teile     1-(3'-Brom-4'-methoxy-phenyl')-          2-methyl-pentanon-(3)    werden in 140 Teilen       94%igem    Alkohol gelöst und nach Zusatz  von 10 Teilen wässeriger 41%iger     Mono-          methylaminlösung    mit 7 Teilen Aluminium  amalgam bei 60 bis 70  behandelt. Bei der       Reduktion    wird das Bromatom     durch    Wasser  stoff ersetzt.

   Nach deren Beendigung wird vom         Aluminiumhydroxydabfiltriert,        dieses    gut mit  Alkohol gewaschen, der Alkohol     abdestilliert     und das     gebildete    sekundäre     Amin    in     ver-          dünnter    Salzsäure gelöst.     Diese    Lösung     wirc     mit Äther von den nicht basischen Bestand  teilen befreit     und        die    Base mit     NatronlaugE     in Freiheit gesetzt.

   Sie     wird    in Äther auf  genommen, die Lösung mit wasserfreiem     Na-          triumsulfat    getrocknet, der Äther     abdestil-          liert    und die freie     Base,    das     1-(4'-Methoxy-          phenyl)-2-methyl-3-methylamino-pentan,    bei  102  und 0,5     mm    Druck im Vakuum destil  liert.



  Process for the preparation of an araliphatic amine. The subject of the present patent is a process for the preparation of an araliphatic amine. The process is characterized in that 1- (3'-halo-4'-methoxyphenyl) -2-methyl-pentanone- (3) is treated with a reducing agent in the presence of monomethylamine,

   with the simultaneous replacement of the halogen by hydrogen, the 3-methylamino derivative of the starting material is formed. The resulting new compound, 1- (4'-1Yethoxyphenyl) -2-methyl-3-methylamino-pentane, boils under 0.5 mm pressure at 102. It should be used as a medicament.



       Example: 20 parts of 1- (3'-bromo-4'-methoxyphenyl ') -2-methyl-pentanone- (3) are dissolved in 140 parts of 94% alcohol and, after adding 10 parts of aqueous 41% mono - methylamine solution treated with 7 parts of aluminum amalgam at 60 to 70. During the reduction, the bromine atom is replaced by hydrogen.

   When this has ended, the aluminum hydroxide is filtered off, washed well 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 sodium sulfate, the ether is distilled off and the free base, 1- (4'-methoxyphenyl) -2-methyl-3-methylamino-pentane, at 102 and 0.5 mm pressure distilled in vacuo.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines aralipha- tischen Amins, dadurch gekennzeichnet., dass man 1-(3'-Ha@ogen-4'-methoxy-phenyl)-2-me- thyl-pentanon-(3) in Gegenwart von Mono- methyl-amin mit einem Reduktionsmittel be handelt. Die entstandene neue Verbindung. das 1-(4'-Methoxy-phenyl)-2-methyl-3-me. thylamino-pentan, siedet unter 0,5 mm Druck bei 102 . Claim: Process for the preparation of an araliphatic amine, characterized in that 1- (3'-Ha @ ogen-4'-methoxy-phenyl) -2-methyl-pentanone- (3) in the presence of mono - methyl-amine is treated with a reducing agent. The resulting new connection. 1- (4'-methoxyphenyl) -2-methyl-3-me. thylamino-pentane, boils under 0.5 mm pressure at 102.
CH252238D 1945-05-08 1945-05-08 Process for the preparation of an araliphatic amine. CH252238A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH252238T 1945-05-08

Publications (1)

Publication Number Publication Date
CH252238A true CH252238A (en) 1947-12-15

Family

ID=4469279

Family Applications (1)

Application Number Title Priority Date Filing Date
CH252238D CH252238A (en) 1945-05-08 1945-05-08 Process for the preparation of an araliphatic amine.

Country Status (1)

Country Link
CH (1) CH252238A (en)

Similar Documents

Publication Publication Date Title
CH252238A (en) Process for the preparation of an araliphatic amine.
CH262486A (en) Process for the preparation of an araliphatic amine.
CH262487A (en) Process for the preparation of an araliphatic amine.
AT94346B (en) Photographic developer.
AT235826B (en) Process for the production of organic peroxides
US2256933A (en) Process for obtaining a substance lowering the blood pressure
AT127820B (en) Process for the preparation of bismuth compounds containing arsenic and antimony.
AT223186B (en) Process for the preparation of new monoalkylaminoalkyloxybenzenes
DE739085C (en) Process for the preparation of ª ‡ -dicarbonyl compounds of the cyclopentanopolyhydrophenanthrene series
CH253185A (en) Process for the preparation of an araliphatic amine.
DE468604C (en) Gelatine for light-sensitive silver salt emulsions and processes for processing ordinary gelatine
AT112135B (en) Process for the preparation of basic oxime ethers and their salts.
AT157699B (en) Method for the preparation of water-soluble organic mercury compounds.
CH300833A (en) Process for the preparation of an N-acyl derivative of iminodibenzyl.
CH261884A (en) Process for the preparation of an araliphatic amine.
DE662035C (en) Process for the production of laxatives
AT208857B (en) Process for the preparation of the new 2,4'-isopentyloxy-phenylimino-3,4 "-isopentyloxy-phenyl-thiazolidine
DE977448C (en) Process for the preparation of 2-phenyl-3-methylmorpholine or its salts which are suitable as medicinal products
CH210974A (en) Process for the production of a new condensation product.
CH255569A (en) Process for the preparation of an araliphatic amine.
CH248378A (en) Process for the preparation of a new oxyhydrophenanthrene derivative.
CH236178A (en) Process for the preparation of p-aminobenzenesulfonyl-butylthiourea.
CH252064A (en) Process for the production of a 4-chloro-phenyl ether.
CH221221A (en) Process for the preparation of 3,5-dimethyl-isoxazole-carboxylic acid- (4) - (N-methyl-anilide).
CH245675A (en) Process for the preparation of 1,2-dimethyl-3-cyano-3-phenyl-pyrrolidine.