CH222736A - Process for the preparation of an aryloxy-alkylamino-butanone. - Google Patents

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

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Publication number
CH222736A
CH222736A CH222736DA CH222736A CH 222736 A CH222736 A CH 222736A CH 222736D A CH222736D A CH 222736DA CH 222736 A CH222736 A CH 222736A
Authority
CH
Switzerland
Prior art keywords
preparation
aryloxy
butanone
alkylamino
parts
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 CH222736A publication Critical patent/CH222736A/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
    • C07D295/10—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 doubly bound oxygen or sulphur atoms
    • C07D295/104—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines     Aryloay-alkylamino-butanons.       Gegenstand des vorliegenden Zusatz  patentes ist ein Verfahren zur Darstellung  eines     Aryloxy-alkylamino-butanons,    dadurch  gekennzeichnet, dass man     Phenoxyaceton    mit  Formaldehyd und     Morpholin    zum     1-Phenoxy-          4-morpholinylbutanon-2    umsetzt.  



  Die neue Verbindung besitzt wertvolle  therapeutische Eigenschaften.  



       Beispiel:     Zur Mischung aus 100 Teilen Monochlor  aceton und 101 Teilen Phenol lässt man un  ter Rühren, bei 20-25  , allmählich 400  Teile 10,7     %ige    Natronlauge laufen. Man  rührt weiter, zuletzt bei<B>50',</B> bis die     wäss-          rige    Schicht neutral reagiert.

   Dann haben  sich 135 bis 145 Teile     Phenoxyaceton    abge  schieden, die abgehoben, mit verdünnter  Lauge gewaschen, getrocknet und destilliert  werden,     Kp.2o    94-98'. 100 Teile davon wer  den mit dem gleichen Volumen Benzol ver  dünnt und diese Lösung bei<B>10'</B> innert einer  Stunde in das kaltbereitete Gemisch aus    68 Teilen     Morpholin,    85 Teilen Benzol und  134 Teilen     Formaldehydlösung    eingerührt.  Man rührt 24     Stunden    bei Raumtemperatur,  weitere 3,     Stunden    bei zuletzt 45  .

   Nach dem  Abkühlen. wird die Base aus dem Reaktions  gemisch mittels verdünnter Schwefelsäure  ausgezogen, nötigenfalls wird die saure     Sul-          fatlösung    durch Extrahieren von etwa noch  beigemengten Resten des neutralen Aus  gangsproduktes befreit, dann eingeengt und  unter Kühlung die freie Base     mittels    Kalium  hydroxyd abgeschieden. Spuren von     Morpho-          lin    werden im Vakuum entfernt.

   Die Aus  beute an     1-Phenoxy-4-morpholinylbutanon-2     beträgt rund 78 % der Theorie, doch werden  über 20 %     Phenoxyaceton    regeneriert; die       Umsetzung    erfolgt demnach, abgesehen vom  geringen Mehrverbrauch an Chloraceton, fast  ohne Materialverlust. Das Produkt bildet  weisse Kristalle (aus Methanol) F. 97  , zeigt  die zu erwartenden Löslichkeiten und lässt  sich als     einsäurige    Base     titrieren    (1 g ver  braucht gegen     Methylorange    40,65 cm'     n/10     Säure, berechnet 40,15 cm').



  Process for the preparation of an aryloay-alkylamino-butanone. The subject of the present additional patent is a process for the preparation of an aryloxy-alkylamino-butanone, characterized in that phenoxyacetone is reacted with formaldehyde and morpholine to give 1-phenoxy-4-morpholinylbutanone-2.



  The new compound has valuable therapeutic properties.



       Example: To a mixture of 100 parts of monochloroacetone and 101 parts of phenol, 400 parts of 10.7% sodium hydroxide solution are gradually run under stirring at 20-25. Stirring is continued, finally at <B> 50 ', </B> until the aqueous layer reacts neutrally.

   Then 135 to 145 parts of phenoxyacetone separated out, which are lifted off, washed with dilute liquor, dried and distilled, bp 20 94-98 '. 100 parts of it are thinned with the same volume of benzene and this solution is stirred into the cold mixture of 68 parts of morpholine, 85 parts of benzene and 134 parts of formaldehyde solution within one hour at <B> 10 '</B>. The mixture is stirred for 24 hours at room temperature, for a further 3 hours at a final 45.

   After cooling down. the base is extracted from the reaction mixture using dilute sulfuric acid, if necessary the acidic sulphate solution is freed by extracting any remaining neutral starting product, then concentrated and the free base is precipitated using potassium hydroxide with cooling. Traces of morpholine are removed in vacuo.

   The yield of 1-phenoxy-4-morpholinylbutanone-2 is around 78% of theory, but over 20% phenoxyacetone is regenerated; the conversion therefore takes place, apart from the slight additional consumption of chloroacetone, with almost no material loss. The product forms white crystals (from methanol) F. 97, shows the expected solubilities and can be titrated as a mono-acidic base (1 g consumed against methyl orange 40.65 cm 'n / 10 acid, calculated 40.15 cm').

Claims (1)

PATENTANSPRUCH Verfahren zur Darstellung eines Aryl- oxy-alkylaminobutanons, dadurch gekenn zeichnet, dass man Phenoxyaceton mit Form ; aldehyd und Morpholin zum 1-Phenoxy-4- morpholinylbutanon-2 umsetzt. PATENT CLAIM Process for the preparation of an aryloxy-alkylaminobutanone, characterized in that phenoxyacetone with form; aldehyde and morpholine converts to 1-phenoxy-4-morpholinylbutanone-2. Das 1-Phenoxy-4-morpholinylbutanon-2 bildet weisse Kristalle (aus Methanol) F. 97 , zeigt die zu erwartenden Löslichkeiten und lässt sich als einsäurige Base titrieren (1 g verbraucht gegen Methylorange 40,65 cm' n/10 Säure, her. 40,15 cm'). Die neue Verbindung besitzt wertvolle therapeutische Eigenschaften. 1-Phenoxy-4-morpholinylbutanone-2 forms white crystals (from methanol) F. 97, shows the solubilities to be expected and can be titrated as a mono-acidic base (1 g consumed against methyl orange 40.65 cm 'n / 10 acid . 40.15 cm '). The new compound has valuable therapeutic properties.
CH222736D 1940-10-08 1940-10-08 Process for the preparation of an aryloxy-alkylamino-butanone. CH222736A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH222736T 1940-10-08
CH552454X 1940-10-08

Publications (1)

Publication Number Publication Date
CH222736A true CH222736A (en) 1942-07-31

Family

ID=25726648

Family Applications (1)

Application Number Title Priority Date Filing Date
CH222736D CH222736A (en) 1940-10-08 1940-10-08 Process for the preparation of an aryloxy-alkylamino-butanone.

Country Status (1)

Country Link
CH (1) CH222736A (en)

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