CH204708A - Process for the preparation of an amino alcohol. - Google Patents

Process for the preparation of an amino alcohol.

Info

Publication number
CH204708A
CH204708A CH204708DA CH204708A CH 204708 A CH204708 A CH 204708A CH 204708D A CH204708D A CH 204708DA CH 204708 A CH204708 A CH 204708A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
alcohol
amino
amino 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 CH204708A publication Critical patent/CH204708A/en

Links

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

Landscapes

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

Description

  

  Verfahren     zur    Darstellung eines     Aminoalkohols.       Das vorliegende Patent betrifft ein Ver  fahren zur Darstellung     eines        Aminealkohols     und     ist    dadurch :gekennzeichnet,     @dass    man       N    -     Methyl        -benzyl-a-aminopropionsäureäthyl-          ester    in Gegenwart eines     Lösungsmittels     reduziert.  



       Das    so erhaltene     d,l-N-Methylbenzylala-          ninol        besitzt,die    Formel  
EMI0001.0016     
    Es ist ein farbloses 01 vom     gp14    = 138 bis  140  .     Es    ist leicht löslich in Alkohol, Äther,  Benzol, dagegen schwer löslich in Wasser.  



  Die neue Verbindung soll     nach    Trennung  in die optisch     aktiven    Komponenten und Ab  spaltung der     Benzylgruppe    zur     Darstellung     von optisch aktiven     Aminoalkoholen    dienen.  <I>Beispiel:</I>  110,5 .g (0,5     Mol)        N-Methyl-benzyl-a-          aminopropionsäureäthylester:     
EMI0001.0027     
    werden in 1 Liter     mit,'iWg-butylat        entwässer-          tem        Butylalkohol    gelöst und die Lösung zum  Sieden erhitzt.

   Nun werden in die siedende  Lösung 100 .g     zerschnittenes    Natrium mög  lichst rasch     eingetragen.    Darauf wird unter  Zusatz     einer    weiteren     Menge        entwässertem          Butylalkohol        weiter    erhitzt, bis alles Metall  gelöst ist. Man lässt abkühlen, versetzt     mit     2-00 g     Fis    und neutralisiert mit     verd.    Salz  säure     (2     : 1) unter guter Aussenkühlung.

   Man  filtriert vom ausgeschiedenen Salz ab und       destilliert    den Alkohol im Vakuum     voll6tän-          dig    ab. Der erhaltene     Rückstand        wird    mit       überschüssiger        Natronlauge    versetzt und     das     in Formeines Öls     ausgeschiedene    rohe     d,l-N-          Methyl-benzylalaninol    in     Äher    aufgenom  men.

   Die Lösung     wird    mit     Glaubersalz    ge  trocknet.     Nach    dem     Abdestillieren    des     Athers          hinterbleibt    ein gefärbter     .Sirup,    der im Va  kuum fraktioniert     wird.       
EMI0002.0001     
  
    Das <SEP> d,1-N-1VIethyl-benzy <SEP> 1-alaniirol <SEP> besitzt
<tb>  die <SEP> Formel     
EMI0002.0002     
    Farbloses<B>01</B> vom     Kp"    =     13,8    bis 140  .       Leicht    löslich in Alkohol, Äther, Benzol.  Schwer     löslieli    in Wasser.

    
EMI0002.0007     
  
    5,263 <SEP> mg <SEP> Substanz <SEP> gaben <SEP> 0,355 <SEP> ein" <SEP> hT, <SEP> <B>(</B>19 <SEP>  , <SEP> <B>749</B> <SEP> mm).
<tb>  0,2893 <SEP> g <SEP> Substanz <SEP> verbrauchten <SEP> 15,76 <SEP> ein' <SEP> n/10 <SEP> HCl <SEP> (= <SEP> 0,0574 <SEP> g <SEP> HCl).
<tb>  C"H,-;ON <SEP> Ber. <SEP> N <SEP> = <SEP> 7,82 <SEP> % <SEP> Mol.=Cew. <SEP> = <SEP> 179.
<tb>  Gef. <SEP> N <SEP> = <SEP> <B>7377</B> <SEP> % <SEP> gol.-Czew. <SEP> =183,6.



  Process for the preparation of an amino alcohol. The present patent relates to a process for the preparation of an amine alcohol and is characterized in that: @that one reduces N - methylbenzyl-a-aminopropionic acid ethyl ester in the presence of a solvent.



       The d, l-N-methylbenzylalaninol thus obtained has the formula
EMI0001.0016
    It is a colorless 01 from gp14 = 138 to 140. It is easily soluble in alcohol, ether and benzene, on the other hand it is sparingly soluble in water.



  After separation into the optically active components and cleavage of the benzyl group, the new compound is intended to be used for the preparation of optically active amino alcohols. <I> Example: </I> 110.5 g (0.5 mol) N-methyl-benzyl-a-aminopropionic acid ethyl ester:
EMI0001.0027
    are dissolved in 1 liter of butyl alcohol dehydrated with "iWg-butylat" and the solution is heated to the boil.

   Now 100 g of cut sodium are added as quickly as possible to the boiling solution. Then, with the addition of a further amount of dehydrated butyl alcohol, heating is continued until all of the metal has dissolved. It is allowed to cool, 2-00 g of Fis are added and the mixture is neutralized 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, l-N-methylbenzylalaninol 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.
EMI0002.0001
  
    The <SEP> d, 1-N-1VIethyl-benzy <SEP> 1-alaniirole <SEP> has
<tb> the <SEP> formula
EMI0002.0002
    Colorless <B> 01 </B> with bp "= 13.8 to 140. Easily soluble in alcohol, ether, benzene. Slightly soluble in water.

    
EMI0002.0007
  
    5.263 <SEP> mg <SEP> substance <SEP> entered <SEP> 0.355 <SEP> "<SEP> hT, <SEP> <B> (</B> 19 <SEP>, <SEP> <B> 749 </B> <SEP> mm).
<tb> 0.2893 <SEP> g <SEP> substance <SEP> consumed <SEP> 15.76 <SEP> a '<SEP> n / 10 <SEP> HCl <SEP> (= <SEP> 0.0574 <SEP> g <SEP> HCl).
<tb> C "H, -; ON <SEP> Ber. <SEP> N <SEP> = <SEP> 7.82 <SEP>% <SEP> Mol. = Cew. <SEP> = <SEP> 179.
<tb> Found <SEP> N <SEP> = <SEP> <B> 7377 </B> <SEP>% <SEP> gol.-Czew. <SEP> = 183.6.

Claims (1)

PATENTANSPRUCII Verfahren zur Darstellung eines Amino- alkohols, dadurch gekennzeichnet, dass man N-llethyl-ben.zyl-a-amino-propionsä,ureäthyl- ester in Gegenwart eines Lösungsmittels reduziert. Das d,1 - N - lllethylbenzy lalaninol besitzt die Formel EMI0002.0017 und ist ein farbloses C)1 vom Kpl4 = 138 bis 140 . A process for the preparation of an amino alcohol, characterized in that N-llethyl-benzyl-a-amino-propionic acid ethyl ester is reduced in the presence of a solvent. The d, 1 - N - Illethylbenzy lalaninol has the formula EMI0002.0017 and is a colorless C) 1 from Kpl4 = 138 to 140. Es ist leicht löslich in Alkohol, Äther, Iierizol, dagegen schwer löslich in Wasser. Die neue Verbindung soll nach Trennung in die optisch aktiven Komponenten und Ab spaltung der Benzylgruppe zur Darstellung von optisch aktiven Aminoalkoholen dienen. It is easily soluble in alcohol, ether, and Iierizol, on the other hand it is hardly soluble in water. After separation into the optically active components and cleavage of the benzyl group, the new compound is intended to serve for the preparation of optically active amino alcohols.
CH204708D 1937-07-21 1937-07-21 Process for the preparation of an amino alcohol. CH204708A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204708T 1937-07-21
CH200996T 1938-11-15

Publications (1)

Publication Number Publication Date
CH204708A true CH204708A (en) 1939-05-15

Family

ID=25723621

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204708D CH204708A (en) 1937-07-21 1937-07-21 Process for the preparation of an amino alcohol.

Country Status (1)

Country Link
CH (1) CH204708A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2573606A (en) * 1946-12-02 1951-10-30 Parke Davis & Co Lower alkyl and alkenyl n-(1-naphthyl methyl) n-hydroxyethyl amines
US2573605A (en) * 1946-12-02 1951-10-30 Parke Davis & Co Tertiary amines and methods for obtaining the same
FR2618148A1 (en) * 1987-07-16 1989-01-20 Adir NOVEL PROCESS FOR THE ENANTIOSPECIFIC PREPARATION OF (S) ETHYLAMINO-2 (TRIFLUOROMETHYL-3-PHENYL) -1 PROPANE

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2573606A (en) * 1946-12-02 1951-10-30 Parke Davis & Co Lower alkyl and alkenyl n-(1-naphthyl methyl) n-hydroxyethyl amines
US2573605A (en) * 1946-12-02 1951-10-30 Parke Davis & Co Tertiary amines and methods for obtaining the same
FR2618148A1 (en) * 1987-07-16 1989-01-20 Adir NOVEL PROCESS FOR THE ENANTIOSPECIFIC PREPARATION OF (S) ETHYLAMINO-2 (TRIFLUOROMETHYL-3-PHENYL) -1 PROPANE
EP0301925A1 (en) * 1987-07-16 1989-02-01 Adir Et Compagnie Process for the enantiospecific preparation of (S)2-ethyl amino-1-3-(trifluoromethyl phenyl) propane
GR880100293A (en) * 1987-07-16 1989-04-12 Adir Novel preparation process of enantiospecific (visually active) s ethylamino-2(trifluoromethyl-3phenyl)-1propane

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