CH204703A - Process for the preparation of an amino alcohol. - Google Patents

Process for the preparation of an amino alcohol.

Info

Publication number
CH204703A
CH204703A CH204703DA CH204703A CH 204703 A CH204703 A CH 204703A CH 204703D A CH204703D A CH 204703DA CH 204703 A CH204703 A CH 204703A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
amino alcohol
optically active
alcohol
Prior art date
Application number
Other languages
German (de)
Inventor
Sandoz Chemische Fabri Vormals
Original Assignee
Chem Fab Vormals Sandoz
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 Chem Fab Vormals Sandoz filed Critical Chem Fab Vormals Sandoz
Publication of CH204703A publication Critical patent/CH204703A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton

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

Description

  

  Verfahren zur Darstellung eines     Aminoalkohols.       Das     vorliegende    Verfahren betrifft die       Darstellung        eines        Aminoalkohols        und.    ist     da-          ,durch    gekennzeichnet,     dass    man a -     Benzyl-          aminoisocapronsäureäthylester    in Gegenwart  eines     Lösungsmittels    reduziert.  



       Das    so erhaltene     d,1-N-Benzylleucinol    der  Formel  
EMI0001.0015     
         kristallisiert    aus     Cyclohegan    in Form von  feinen Nadeln vom     !Smp.    61     bis,63      C.  



  Die neue     Verbigdung    soll nach Trennung  in die optisch aktiven Bestandteile und Ab  spaltung der     Ben.zylgruppe    zur     Darstellung     von     optisch    aktiven     Amrinoalkoholen    dienen.    <I>Beispiel:</I>    124,5     g    a -     Benzylaminoisocapronsäure-          äthylester    (0,5     Mol.)    werden in 1 Liter mit       M-butylat    entwässertem     Butylalkohol        gelöst-          23     und die Lösung zum Sieden erhitzt.

   Nun  werden in die siedende Lösung 100 g zer-         schnittenes    Natrium möglichst     rasch    einge  tragen. Darauf wird     unter    Zusatz einer wei  teren Menge     entwässertem        Butylalkohol    wei  ter erhitzt, bis     alles        Metall    gelöst     ist.    Man  lässt abkühlen, versetzt mit 200     .g        Eis    und  neutralisiert mit     verd..Salzsäure    (2 :

   1)     unter     guter     Aussenkühlung.    Man     filtriert    vom     aus-          gesehiedenen    .Salz ab und destilliert den  Alkohol im Vakuum vollständig ab. Der er  haltene     Rückstand    wird mit überschüssiger  Natronlauge versetzt und das in Form eines  Öls     ausgeschiedene    rohe     d,1-N-Benzylleucinol     in Äther aufgenommen. Die     Lösung    wird mit  Glaubersalz getrocknet.

   Nach dem     Abdestil-          lieren    des Äthers     hinterbleibt    ein gefärbter  Sirup, .der im Vakuum fraktioniert     wird.     



  Das reine     d,1-N-Benzylleucinol    der Formel  
EMI0001.0058     
    destilliert bei 170 bis l:72      /16    mm     Hg    als  farbloses Öl, das bald     vollständig        kristalli-          nisch        erstarrt.    Nach dem     Umkristallisleren         aus     Cyclohexan    erhält man feine Nadeln  vom     Smp.    61     bis   <B>63'</B> C. Das d,l-N-Benzyl-         leucinol    ist     schwer    löslich in Wasser, leicht  löslich in Alkohol, Äther, Benzol.

    
EMI0002.0006     
  
    4,418 <SEP> mb <SEP> Substanz <SEP> gaben <SEP> 0,263 <SEP> ,ein' <SEP> N= <SEP> (21 <SEP>  , <SEP> 750 <SEP> mm)
<tb>  0,2163 <SEP> g <SEP> Substanz <SEP> verbrauchten <SEP> 10,58 <SEP> em3 <SEP> n/10 <SEP> HCl
<tb>  C"1H,1ON <SEP> Ber. <SEP> N <SEP> = <SEP> 6,76 <SEP> % <SEP> Mol.-Gew. <SEP> 207
<tb>  Gef. <SEP> N <SEP> = <SEP> 6,82 <SEP> % <SEP> MOl.-Gew. <SEP> 204,4.       Chlorhydrat:     ,Smp.    = 151 bis<B>153'.</B> Pris  men aus     @Vasser.    Ziemlich schwer löslich in  Wasser.  



       Pikrat:        Smp.    = 152     bis    154  . Gelbes  Prismen aus Alkohol. Schwer löslich in  Wasser.



  Process for the preparation of an amino alcohol. The present process relates to the preparation of an amino alcohol and. is characterized by the fact that a - benzylaminoisocaproic acid ethyl ester is reduced in the presence of a solvent.



       The thus obtained d, 1-N-benzylleucinol of the formula
EMI0001.0015
         crystallized from cyclohegan in the form of fine needles of! 61 to, 63 C.



  After separation into the optically active constituents and splitting of the benzyl group, the new compound is intended to be used for the preparation of optically active amino alcohols. <I> Example: </I> 124.5 g of a - benzylaminoisocaproic acid ethyl ester (0.5 mol.) Are dissolved in 1 liter of butyl alcohol dehydrated with M-butoxide and the solution is heated to the boil.

   100 g of cut sodium are now introduced into the boiling solution as quickly as possible. Then, with the addition of a further amount of dehydrated butyl alcohol, heating is continued until all of the metal has dissolved. Allow to cool, add 200 g of ice and neutralize with dilute hydrochloric acid (2:

   1) with good external cooling. The precipitated salt is filtered off and the alcohol is completely distilled off in vacuo. The residue obtained is mixed with excess sodium hydroxide solution and the crude d, 1-N-benzylleucinol which has separated out in the form of an oil is taken up in ether. The solution is dried with Glauber's salt.

   After the ether has been distilled off, a colored syrup remains, which is fractionated in a vacuum.



  The pure d, 1-N-Benzylleucinol of the formula
EMI0001.0058
    distilled at 170 to 1: 72/16 mm Hg as a colorless oil which soon solidifies completely in a crystalline manner. After recrystallization from cyclohexane, fine needles with a melting point of 61 to 63 ° C. The d, l-N-benzylleucinol is sparingly soluble in water, easily soluble in alcohol, ether, benzene.

    
EMI0002.0006
  
    4.418 <SEP> mb <SEP> substance <SEP> entered <SEP> 0.263 <SEP>, a '<SEP> N = <SEP> (21 <SEP>, <SEP> 750 <SEP> mm)
<tb> 0.2163 <SEP> g <SEP> substance <SEP> used <SEP> 10.58 <SEP> em3 <SEP> n / 10 <SEP> HCl
<tb> C "1H, 1ON <SEP> range <SEP> N <SEP> = <SEP> 6.76 <SEP>% <SEP> molar weight <SEP> 207
<tb> Gef. <SEP> N <SEP> = <SEP> 6.82 <SEP>% <SEP> MOl.- wt. <SEP> 204.4. Hydrochloride:, m.p. = 151 to <B> 153 '. </B> Prisms from @Vasser. Fairly sparingly soluble in water.



       Picrate: m.p. = 152 to 154. Yellow prisms made of alcohol. Slightly soluble in water.

Claims (1)

PATEN TANSPRUCI3 Verfahren zur Darstellung eines Amino- alkohols, dadurch gekennzeichnet, dass man u-Benzylaminoisocapronsäureäthylester in Ge genwart eines Lösungsmittels reduziert. Das d,1-N-Berizylleueinol der Formel EMI0002.0020 kristallisiert aus Cy clohexan in Form von feinen Nadeln vom Smp. 61 bis 63 C. PATEN TANSPRUCI3 Process for the preparation of an amino alcohol, characterized in that ethyl u-benzylaminoisocaproate is reduced in the presence of a solvent. The d, 1-N-bericylleueinol of the formula EMI0002.0020 crystallized from cyclohexane in the form of fine needles with a melting point of 61 to 63 C. Die neue Verbindung .soll nach Trennung in die optisch aktiven Bestandteile und<B>Ab-</B> spaltung der Benzylgruppe zur Darstellung von optisch aktiven Aminoa.lkoholen dienen. The new compound should, after separation into the optically active components and <B> cleavage </B> of the benzyl group, be used to prepare optically active amino alcohols.
CH204703D 1937-07-21 1937-07-21 Process for the preparation of an amino alcohol. CH204703A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204703T 1937-07-21
CH200996T 1938-11-15

Publications (1)

Publication Number Publication Date
CH204703A true CH204703A (en) 1939-05-15

Family

ID=25723616

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204703D CH204703A (en) 1937-07-21 1937-07-21 Process for the preparation of an amino alcohol.

Country Status (1)

Country Link
CH (1) CH204703A (en)

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