CH269082A - Process for the preparation of a diaryl-butenyl-amine. - Google Patents

Process for the preparation of a diaryl-butenyl-amine.

Info

Publication number
CH269082A
CH269082A CH269082DA CH269082A CH 269082 A CH269082 A CH 269082A CH 269082D A CH269082D A CH 269082DA CH 269082 A CH269082 A CH 269082A
Authority
CH
Switzerland
Prior art keywords
diethylamino
compound
preparation
diaryl
butenyl
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 CH269082A publication Critical patent/CH269082A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups

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

Description

         

  Verfahren zur Herstellung eines     DiaryI-butenyl-amins.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines     Diaryl-          butenyl-amins.    Das Verfahren ist dadurch  gekennzeichnet,     dass    man aus einer Verbin  dung der Formel  
EMI0001.0005     
    wobei X einen zusammen mit einem Wasser  stoffatom unter Bildung der Verbindung     HX          abspaltbaren    Rest bedeutet, zwecks Einfüh  rung einer Doppelbindung die Verbindung       HX    abspaltet,  Die erhaltene neue Verbindung, ein     Di-          äthylamino-diphenyl-buten,    siedet unter  <B>0,

  3</B> mm Druck bei     141-142'.    Ihr     Hydroehlorid     schmilzt bei     112-115'.    Die neue Base soll  therapeutische Verwendung finden.  



  <I>Beispiel<B>1:</B></I>  <B>29,7</B> Teile     1,2-Diphenyl-4-diäth.ylamino-          butanol-(2)        werden        mit        130        Teilen        80%iger     Phosphorsäure<B>1</B> Stunde     auf   <B>130-1350</B> er  wärmt.

   Nach Abkühlen wird mit Wasser     ver-          dÜnnt,    durch vorsichtige Zugabe von     krist.          INlatriumearbonat    alkalisch gestellt und das  ausgeschiedene basische<B>Öl</B> in Äther aufge  nommen; nach Trocknen der Ätherlösung mit  geglühter     Pottasehe    und Abdampfen des Lö-         sungsmittels    destilliert man die rohe Base.       Man    erhält in guter Ausbeute das     Diäthyl-          amino-diphenyl-buten    als schwach gefärbtes  <B>Öl</B> vom Siedepunkt     141-14211    bei<B>0,3</B> mm.  



  <I>Beispiel 2:</I>  Eine Lösung von<B>29,7</B> Teilen     1,2-Diphenyl-          4-diäthylamino-b-Litanol-(2)    in<B>150</B> Teilen  Chloroform wird zunächst mit trockenem       Salzsäuregas    bis zur deutlich kongosauren  Reaktion behandelt, hierauf mit 12 Teilen       Thionylehlorid    versetzt und dann<B>1</B> Stunde  bei Raumtemperatur und<B>3</B> Stunden bei<B>50'</B>  gerührt.

   Man destilliert das Lösungsmittel  unter vermindertem Druck ab und erhitzt  den Rückstand mit<B>150</B> Teilen     Dimethyl-          anilin        auf        180-190'.    Nach Zugabe von     wäss-          riger    Natronlauge wird das     Dimethylanilin     mit Wasserdampf     abdestilliert.    Der Rück  stand wird mit Benzol ausgeschüttelt.

   Aus der  abgetrennten     Benzollösung    werden die ba  sischen Anteile mit verdünnter Schwefelsäure  ausgezogen, Nach     Alkalischstellen    des mineral  sauren Auszuges mit Natronlauge, Abtrennen  des dabei sich abscheidenden basischen Öls  und     Troeknen    über geglühter Pottasche erhält  man in guter Ausbeute das     Diäthylamino-          diphenyl-buten    als fast farbloses<B>Öl</B> 'vom  Siedepunkt 141-1420 bei<B>0,3</B>     mm    Druck.



  Process for the preparation of a diaryi-butenyl-amine. The present patent relates to a process for the preparation of a diaryl-butenylamine. The process is characterized in that a compound of the formula
EMI0001.0005
    where X denotes a radical which can be split off together with a hydrogen atom to form the compound HX, the compound HX splits off for the purpose of introducing a double bond, the new compound obtained, a diethylamino-diphenyl-butene, boils below <B> 0,

  3 mm print at 141-142 '. Your hydrochloride melts at 112-115 '. The new base is to be used therapeutically.



  <I>Example<B>1:</B> </I> <B> 29.7 </B> parts 1,2-diphenyl-4-diethylamino-butanol- (2) with 130 parts 80 % phosphoric acid <B> 1 </B> hour to <B> 130-1350 </B> it warms up.

   After cooling, it is diluted with water by careful addition of crystalline. INsodium carbonate made alkaline and the excreted basic <B> oil </B> taken up in ether; after the ether solution has been dried with calcined potatoes and the solvent has been evaporated off, the crude base is distilled. Diethylamino-diphenyl-butene is obtained in good yield as a weakly colored oil with a boiling point of 141-14211 at 0.3 mm.



  <I> Example 2: </I> A solution of <B> 29.7 </B> parts of 1,2-diphenyl-4-diethylamino-b-litanol- (2) in <B> 150 </B> Parts of chloroform are first treated with dry hydrochloric acid gas until the reaction is clearly Congo acid, then 12 parts of thionyl chloride are added and then <B> 1 </B> hour at room temperature and <B> 3 </B> hours at <B> 50 '< / B> stirred.

   The solvent is distilled off under reduced pressure and the residue is heated to 180-190 'with 150 parts of dimethylaniline. After adding aqueous sodium hydroxide solution, the dimethylaniline is distilled off with steam. The residue is extracted with benzene.

   The basic components are extracted from the separated benzene solution with dilute sulfuric acid. After making the mineral acid extract alkaline with sodium hydroxide solution, separating the basic oil which separates out and drying it over the calcined potash, the diethylaminodiphenylbutene is obtained in good yield as an almost colorless < B> Oil </B> 'with a boiling point of 141-1420 at <B> 0.3 </B> mm pressure.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Diaryl- butenyl-amins, dadurch gekennzeichnet, dass man aus einer Verbindung der Formel EMI0002.0001 wobei X einen zusammen mit einem Wasser stoffatom unter Bildung der Verbindung HX abspaltbaren Rest bedeutet, zwecks Einfüh- rang einer Doppelbindung die Verbindung HX abspaltet. PATENT CLAIM: Process for the preparation of a diaryl-butenyl-amine, characterized in that a compound of the formula EMI0002.0001 where X denotes a radical which can be split off together with a hydrogen atom to form the compound HX, the compound HX splits off for the purpose of introducing a double bond. Die erhaltene neue Verbindung, ein Di- ätl-lylamino <B>-</B> diphenyl <B>-</B> bLiten, siedet unter <B>0,3</B> mm Druck bei 141-142'. Ihr Hydrochlorid schmilzt bei 112-1151. <B>UNTERANSPRÜCHE:</B> <B>1.</B> Verfahren nach Patentanspr-Lieh, da durch gekennzeichnet, dass man 1,2-Diphenyl- 4-diäthylamino-b-titanol- (2) mit einem wasser abspaltenden Mittel behandelt. The new compound obtained, a diethylamino <B> - </B> diphenyl <B> - </B> bLiten, boils under <B> 0.3 </B> mm pressure at 141-142 '. Its hydrochloride melts at 112-1151. <B> SUBClaims: </B> <B> 1. </B> Method according to patent claim Lieh, characterized in that 1,2-diphenyl-4-diethylamino-b-titanol- (2) with a water treated with separating agents. 2.'Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man aus einem 1,2-Dipheliyl-4-diäthylamino-butanol- (2) -ester durch Einwirkung einer Base die Säure ab spaltet. 2.'Verfahren according to claim, characterized in that the acid is split off from a 1,2-dipheliyl-4-diethylamino-butanol (2) ester by the action of a base.
CH269082D 1947-09-05 1947-09-05 Process for the preparation of a diaryl-butenyl-amine. CH269082A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH265665T 1947-09-05
CH269082T 1947-09-05

Publications (1)

Publication Number Publication Date
CH269082A true CH269082A (en) 1950-06-15

Family

ID=25730819

Family Applications (1)

Application Number Title Priority Date Filing Date
CH269082D CH269082A (en) 1947-09-05 1947-09-05 Process for the preparation of a diaryl-butenyl-amine.

Country Status (1)

Country Link
CH (1) CH269082A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0080721A3 (en) * 1981-11-30 1983-08-24 Sumitomo Chemical Company, Limited Diphenylalkanoamine derivatives, and their production and use

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0080721A3 (en) * 1981-11-30 1983-08-24 Sumitomo Chemical Company, Limited Diphenylalkanoamine derivatives, and their production and use

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