CH222741A - Process for the preparation of an aryloxy-alkylamino-butanol. - Google Patents

Process for the preparation of an aryloxy-alkylamino-butanol.

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Publication number
CH222741A
CH222741A CH222741DA CH222741A CH 222741 A CH222741 A CH 222741A CH 222741D A CH222741D A CH 222741DA CH 222741 A CH222741 A CH 222741A
Authority
CH
Switzerland
Prior art keywords
methoxyphenoxy
preparation
alkylamino
aryloxy
butanol
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH222741A publication Critical patent/CH222741A/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
    • C07D295/08—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 bound oxygen or sulfur atoms
    • C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

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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     Aryloxy-alkylamino-butanols.       Gegenstand des     vorliegenden:    Zusatz  patentes ist ein Verfahren zur Darstellung  eines     Aryloxy-alkylamino-butanols,    dadurch  gekennzeichnet, dass man     (2'-Methoxy-phen-          oxy-l')-aceton    mit Formaldehyd und     Mor-          pholin    zum     1-(2'-Methoxy-phenoxy-1')-4-          morpholinyl-butanon-2    umsetzt und diese  Verbindung zum entsprechenden sekundären  Alkohol reduziert.  



  Die neue Verbindung besitzt wertvolle  therapeutische Eigenschaften.  



  <I>Beispiel:</I>  68 Teile     Morpholin,    in 85 Teilen Benzol  gelöst, werden unter Vermeidung einer Tem  peraturerhöhung mit 134 Teilen 29%iger       Formaldehydlösung    versetzt. Nach längerem  Stehen lässt man unter Rühren innert einer  Stunde 120 Teile     Guajacoxy-aceton    oder     (2'-          Methoxy-phenoxy-1')-aceton    (aus     Guajacol     und Chloraceton     in    verdünnter Lauge herge  stellt,     Kp."    =     96-98')    verdünnt mit dem  gleichen Volumen Benzol, einfliessen, wobei  die Temperatur auf ca.<B>10'</B>     gehalten    wird.

      Man rührt weitere 24     Stunden    ohne Küh  lung, erwärmt dann auf 40-45   und hält  dabei noch 3 Stunden. Nach dem Abkühlen       wird    die Base aus dem     Reaktionsgemisch          mittels    verdünnter Schwefelsäure ausgezo  gen, nötigenfalls wird die saure     Sulfatlösung     durch Extrahieren von etwa noch beigemeng  ten. Resten des neutralen Ausgangsproduktes  befreit, dann eingeengt und unter Kühlung  die freie Base mittels     Kaliumhydroxyd    abge  schieden.     Spuren    von     Morpholin    werden im  Vakuum     entfernt.     



  Das Produkt     1-(2'-Methoxy-phenoxy-1')-          4-morpholinylbutanon-2    ist bei gewöhnlicher  Temperatur eine schwach     gelbstichig    ge  färbte Flüssigkeit, die sich beim     Titrieren    als       einsäurige    Base erweist. Die Salze sind in  Wasser spielend leicht löslich, das Hydro  chlorid, weisse bei 148-1501 schmelzende  Kristalle, ist äusserst hygroskopisch.  



  Zwecks     Reduktion    des     Aminoketons    löst  man es in der zehn- bis zwölffachen Menge  absolutem Alkohol, gibt zur siedenden Lö  sung, unter Durchleiten von Stickstoff, all-           inählich    ein     f)rillel    des     Ketongewichtes    an  Natrium, rührt die entstehende Suspension       iiiid    gibt nach und nach noch ein oder zwei  Drittel     Natrium    zu.  



  Nach beendeter     Reduktion    wird das auf  abgekühlte     Reaktionsgemisch    mit eis  kalter,     halbverdünnter    Salzsäure schwach       überneutralisiert,    das abgeschiedene Koch  salz entfernt     und    der Alkohol     iin    Vakuum       ah(letilliert.    Die Verbindung, das     1-(2'-Me-          tlioxy-l)lienoxy-1')-4-niorpholinylliutanol-2    ist.

    eine viskose. schwer kristallisierende Masse,  leicht löslich in     den        geliräuclilichen        Solven-          iien    und in Säuren, mit denen sie gut kristal  lisierende, leicht lösliche Salze bildet,     Hy-          drochlorid    F. unter Zersetzung um 160  . 1 g       verbraucht    gegen     Hethylorange        36,0    cm'       n/1        (l    Säure, berechnet 35,8 cm'.



  Process for the preparation of an aryloxy-alkylamino-butanol. Subject of the present: Additional patent is a process for the preparation of an aryloxy-alkylamino-butanol, characterized in that (2'-methoxy-phenoxy-1 ') - acetone with formaldehyde and morpholine to 1- (2' -Methoxy-phenoxy-1 ') -4-morpholinyl-butanone-2 and this compound is reduced to the corresponding secondary alcohol.



  The new compound has valuable therapeutic properties.



  <I> Example: </I> 68 parts of morpholine, dissolved in 85 parts of benzene, are mixed with 134 parts of 29% strength formaldehyde solution while avoiding an increase in temperature. After standing for a long time, 120 parts of guaiaxoxy-acetone or (2'-methoxyphenoxy-1 ') -acetone (made from guaiacol and chloroacetone in dilute lye, b.p. "= 96-98") are diluted with stirring within one hour with the same volume of benzene, while the temperature is kept at about <B> 10 '</B>.

      The mixture is stirred for a further 24 hours without cooling, then heated to 40-45 and held for a further 3 hours. After cooling, the base is extracted from the reaction mixture using dilute sulfuric acid, if necessary the acidic sulfate solution is freed by extracting any remaining neutral starting product, then concentrated and the free base separated using potassium hydroxide with cooling. Traces of morpholine are removed in vacuo.



  The product 1- (2'-methoxyphenoxy-1 ') -4-morpholinylbutanone-2 is a slightly yellow-tinged liquid at normal temperature, which turns out to be a mono-acidic base when titrated. The salts are easily soluble in water, the hydrochloride, white crystals melting at 148-1501, is extremely hygroscopic.



  To reduce the aminoketone, dissolve it in ten to twelve times the amount of absolute alcohol, add a f) millel of the weight of the ketone weight of sodium to the boiling solution while passing nitrogen through it, and stir the resulting suspension iiiid little by little one or two thirds of sodium too.



  After the reduction is complete, the cooled reaction mixture is slightly over-neutralized with ice-cold, semi-dilute hydrochloric acid, the precipitated common salt is removed and the alcohol is letillated in vacuo. The compound 1- (2'-methyl-oxy-1) lienoxy-1 ') Is -4-niorpholinylliutanol-2.

    a viscous one. Difficult to crystallize mass, easily soluble in the gelatinous solvents and in acids with which it forms well crystallizing, easily soluble salts, hydrochloride F. with decomposition around 160. 1 g consumed against methyl orange 36.0 cm 'n / 1 (l acid, calculated 35.8 cm'.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Aryloxy- alkylaminobutaliols, dadurch gekennzeichnet, dass man (2'-Methoxy-phenoxy-1')-aceton mit Formaldehyd und Morpholin zum 1-(2'-Me- thoxy- phenoxy-1')-4 - morpholinylbutanon- 2 umsetzt und diese Verbindung zum entspre chenden sekundären Alkohol reduziert. PATENT CLAIM: Process for the preparation of an aryloxyalkylaminobutaliol, characterized in that (2'-methoxyphenoxy-1 ') - acetone with formaldehyde and morpholine to give 1- (2'-methoxyphenoxy-1') - 4 - Morpholinylbutanon- 2 converts and this compound is reduced to the corresponding secondary alcohol. Das 1-(2'-Methoxy-phenoxy-1')-4-niorpho- liuy lliutanol-\2 ist eine viskose, schwer kri stallisierende Masse, leicht löslich in den ge bräuchlichen Solventien und in Säuren, mit denen sie gilt kristallisierende, leicht lösliche Salze bildet. Hydrochlorid F. unter Zer setzung um<B>160'.</B> 1 g verbraucht gegen Me- thylorange 36,0 cmg n/10 Säure, berechnet 35,8 cm 8. Die neue Verbindung besitzt wertvolle therapeutische Eigenschaften. The 1- (2'-methoxyphenoxy-1 ') -4-niorpholiuy lliutanol- \ 2 is a viscous, difficult to crystallize mass, easily soluble in the common solvents and in acids with which it applies crystallizing, forms easily soluble salts. Hydrochloride F. decomposed by <B> 160 '. </B> 1 g consumed against methyl orange 36.0 cmg n / 10 acid, calculated 35.8 cm 8. The new compound has valuable therapeutic properties.
CH222741D 1940-10-08 1940-10-08 Process for the preparation of an aryloxy-alkylamino-butanol. CH222741A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH222741T 1940-10-08
CH552454X 1940-10-08

Publications (1)

Publication Number Publication Date
CH222741A true CH222741A (en) 1942-07-31

Family

ID=25726653

Family Applications (1)

Application Number Title Priority Date Filing Date
CH222741D CH222741A (en) 1940-10-08 1940-10-08 Process for the preparation of an aryloxy-alkylamino-butanol.

Country Status (1)

Country Link
CH (1) CH222741A (en)

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