CH227888A - Process for the preparation of a higher amine. - Google Patents

Process for the preparation of a higher amine.

Info

Publication number
CH227888A
CH227888A CH227888DA CH227888A CH 227888 A CH227888 A CH 227888A CH 227888D A CH227888D A CH 227888DA CH 227888 A CH227888 A CH 227888A
Authority
CH
Switzerland
Prior art keywords
morpholine
ethyl
preparation
phenyl
mole
Prior art date
Application number
Other languages
German (de)
Inventor
Albert Chemische Werke
Original Assignee
Albert Ag Chem Werke
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 Albert Ag Chem Werke filed Critical Albert Ag Chem Werke
Publication of CH227888A publication Critical patent/CH227888A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

  

  Verfahren zur Herstellung eines höheren Amins.    Es     wurde,    gefunden, dass man zu thera  peutisch wertvollen Verbindungen gelangen  kann, wenn man auf 1     Mol        l,@-Di-plienyl-          äthyl-amin        lvIoi@pliolinoalkyllialogenide    einwir  ken lässt. Von besonderem Vorteil hat sich  hierbei erwiesen, wenn man beim Umsetzen  des     ilIorpliolinoalkylhalogenids    mit dein Aus  gangsamin 1     Mol    einer     tertiären    Base (vor  teilhafterweise     Triäthanolamin)    zusetzt, um  auf diese Weise die, in der Reaktion ent  stehende     Halogenwasserstoffsäure    abzufangen.  



       Gegenstand    des vorliegenden Patentes ist  ein Verfahren zur Herstellung<I>von</I>       Di-pheiiyl-ätliylamino)-äthyll-morpholin,    das  dadurch gekennzeichnet ist, dass man     äqui-          molekulare    Mengen     ,8,P-Di-phenyl-äthylamiii     und     4-(p-Halogen-äthyl)-morpholin    aufeinander  einwirken lässt. Es kann dabei zum     Abfangen     der bei der Reaktion     entstehenden        Halogen-          wasserstoffsäure    1     Mol    einer tertiären Base  hinzugefügt werden.  



  Das     Bihydrochlorid    des so erhaltenen     4-          [@-(@',3'-Diplienyl    -     äthy        lamirio)-        äthyl]-    morpho-         lin    bildet weisse, körnige     Kristalle    vom       Schmelzpunkt    202  .

      <I>Beispiel:</I>         ss,ss-Diphenyläthyl        -morpholin        oäthyl    -     amin.     1     Mol        P,ss-Di-phenyl-äthylamin,    1     Mol        4-(@-          Chlor-äthyl)-morpholin    und 1     Mol        Triäthanol-          amin    werden eine Stunde am     Rückflusskühler     auf dem siedenden Wasserbad erhitzt, wobei  unter Gelb- bis Rotfärbung     Abscheidung    von       Triäthanolamin-hydrochlorid    eintritt.

   Man ver  setzt mit Wasser,     nimmt    das<B>01</B> in Äther auf  und fällt nach dem Trocknen mit     Ätzkali     mit ätherischer Salzsäure. Das ausfallende       Bihydrochlorid    wird durch     Umkristallisieren     aus Methanol und eventuelles     Fällen    mit  Äther     gereinigt.     



       Bihydrochlorid:    weisse, körnige Kristalle  vom     Schmelzpunkt    2021.



  Process for the preparation of a higher amine. It has been found that therapeutically valuable compounds can be obtained if one can act on 1 mol of l, @ - di-plienyl ethyl amine lvIoi @ pliolinoalkyllialogenide. It has been found to be of particular advantage if 1 mol of a tertiary base (before geous triethanolamine) is added when the ilIorpliolinoalkylhalogenids are reacted with the starting amine, in order to trap the hydrohalic acid produced in the reaction.



       The subject of the present patent is a process for the production of di-pheiiyl-ätliylamino) -äthyll-morpholine, which is characterized in that equimolecular amounts, 8, P-di-phenyl-ethylamiii and 4- (p-halo-ethyl) -morpholine can act on each other. In this case, 1 mol of a tertiary base can be added to trap the hydrohalogen acid formed in the reaction.



  The bihydrochloride of the 4- [@ - (@ ', 3'-diplienyl - ethy lamirio) - ethyl] - morpholine thus obtained forms white, granular crystals with a melting point of 202.

      <I> Example: </I> ss, ss-Diphenyläthyl -morpholin oäthyl - amine. 1 mole of P, ß-di-phenyl-ethylamine, 1 mole of 4 - (@ - chloro-ethyl) -morpholine and 1 mole of triethanolamine are heated on the reflux condenser on the boiling water bath for one hour, with a yellow to red color separation of Triethanolamine hydrochloride occurs.

   It is mixed with water, the <B> 01 </B> is absorbed in ether and, after drying, it is precipitated with caustic potash with ethereal hydrochloric acid. The precipitated bihydrochloride is purified by recrystallization from methanol and possibly precipitation with ether.



       Bihydrochloride: white, granular crystals with a melting point of 2021.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 4-(R-(ss',(@'- Di-phenyl-äthylamino)-äthyl]-morpholin, da- durch gekennzeichnet, dass man äquimoleku- lare Mengen P,P-Di-phenyl-äthylamin und .1- (f3-Halogen-äthyl)-morpholin aufeinander ein wirken lässt. Das Dichlorhydrat der neuen Verbindung hat den Schmelzpunkt 202'. PATENT CLAIM: Process for the preparation of 4- (R- (ss ', (@' - Di-phenyl-ethylamino) -ethyl] -morpholine, characterized in that equimolecular amounts of P, P-di-phenyl- ethylamine and .1- (f3-halo-ethyl) -morpholine interact. The dichlorohydrate of the new compound has a melting point of 202 '. Uh TERÄN SPRUCI3 Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man dem Umsetzungs gemisch 1 Mol einer tertiären Base zum Ab fangen der entstehenden Halogenwasserstoff- Säure zusetzt. Uh TERÄN SPRUCI3 Process according to patent claim, characterized in that 1 mole of a tertiary base is added to the reaction mixture to catch the resulting hydrohalic acid.
CH227888D 1942-02-25 1942-02-25 Process for the preparation of a higher amine. CH227888A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH227888T 1942-02-25

Publications (1)

Publication Number Publication Date
CH227888A true CH227888A (en) 1943-07-15

Family

ID=4455297

Family Applications (1)

Application Number Title Priority Date Filing Date
CH227888D CH227888A (en) 1942-02-25 1942-02-25 Process for the preparation of a higher amine.

Country Status (1)

Country Link
CH (1) CH227888A (en)

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