CH186667A - Process for the preparation of 1-phenyl-N-methyl-N-6'-methoxy-3'-methyl-benzyl-2-aminopropanol-1-chlorohydrate. - Google Patents

Process for the preparation of 1-phenyl-N-methyl-N-6'-methoxy-3'-methyl-benzyl-2-aminopropanol-1-chlorohydrate.

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Publication number
CH186667A
CH186667A CH186667DA CH186667A CH 186667 A CH186667 A CH 186667A CH 186667D A CH186667D A CH 186667DA CH 186667 A CH186667 A CH 186667A
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CH
Switzerland
Prior art keywords
methyl
phenyl
aminopropanol
chlorohydrate
benzyl
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH186667A publication Critical patent/CH186667A/en

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Description

  

  Verfahren zur Herstellung von     1-Phenyl-N-methyl-N-6'-methoxy-3'-methyl-          benzyl-2-amino-propanol-l-chlor        hydrat.       Es wurde     gefunden,    dass man     Aminoalko-          hole    der allgemeinen Formel  
EMI0001.0007     
    worin X Wasserstoff oder einen     Alkylrest,     Y einen durch     verätherte    oder veresterte       Hydroxylgruppen    substituierten     Benzylrest     bedeutet, dadurch herstellen kann, dass man  entweder die den     Aminoalkoholen    entspre  chenden     Benzylaminoketone    reduziert,

   oder  in die entsprechenden primären oder sekun  dären     Aminoalkohole    einen durch     verätherte     oder veresterte     1Tydroxylgruppen        substituier-          ten        Benzylrest    einführt.  



  Gegenstand des vorliegenden     Patentes    ist  ein Verfahren zur     Herstellung    von     1-Phenyl-          N-methy    1-N- 6'-methoxy-3'-methylbenzyl-2-         aminopropanol-l-chlorhydrat    von folgender  Formel:  
EMI0001.0025     
    welches dadurch gekennzeichnet ist, dass man       3-Methyl-6-methoxybenzylchlorid    mit     1-Phe-          nyl-2-methylamino-propanol-1        umsetzt.    Das  Endprodukt bildet farblose     Kristalle,    welche  in Wasser und Alkohol     ziemlich    schwer lös  lich sind.

   Es zeichnet sich durch eine hervor  ragende krampflösende     Wirkung    auf     Spas-          men    der Bronchien, Gallenwege und     Darm     aus, welche die des bekannten     1-Phenyl-2-          benzylmethyl-aminopropanols    um ein Mehr  faches übertrifft.      <I>Beispiel:</I>  85 g     3-Methyl-6-methogybenzylchlorid,     165 g     1-Phenyl-2-methylamino-propanol-1     werden in 1000     cni3    Benzol einige     .Stunden     auf dem     Wasserbad    gekocht.

   Von dem aus  geschiedenen salzsauren     Phenylmethylamino-          propanol    wird     abfiltriert,        die        Benzollösung     mit alkoholischer Salzsäure neutralisiert und  dann     filtriert.    Das erhaltene     1-Phenyl-N-          methyl    - N -     V    -     methogy    -     3'-        methylbenzyl    -     2-          aminopropanol-l-chlorhydrat    wird aus Al  kohol     umkristallisiert.    Schmelzpunkt 207 bis       209' 

      C. Die Ausbeute ist nahezu     quantitativ.     Das Endprodukt bildet farblose Kristalle,    welche in     Wasser        und    Alkohol     ziemlich     schwer löslich sind.



  Process for the preparation of 1-phenyl-N-methyl-N-6'-methoxy-3'-methyl-benzyl-2-aminopropanol-1-chlorohydrate. It has been found that amino alcohols of the general formula
EMI0001.0007
    where X is hydrogen or an alkyl radical, Y is a benzyl radical substituted by etherified or esterified hydroxyl groups, can be prepared by either reducing the benzylaminoketones corresponding to the amino alcohols,

   or introduces a benzyl radical substituted by etherified or esterified hydroxyl groups into the corresponding primary or secondary amino alcohols.



  The subject of the present patent is a process for the preparation of 1-phenyl-N-methy 1-N- 6'-methoxy-3'-methylbenzyl-2-aminopropanol-1-chlorohydrate of the following formula:
EMI0001.0025
    which is characterized in that 3-methyl-6-methoxybenzyl chloride is reacted with 1-phenyl-2-methylamino-propanol-1. The end product forms colorless crystals, which are rather sparingly soluble in water and alcohol.

   It is characterized by an excellent antispasmodic effect on spasms of the bronchi, biliary tract and intestines, which is several times greater than that of the well-known 1-phenyl-2-benzylmethyl-aminopropanol. <I> Example: </I> 85 g of 3-methyl-6-methogybenzyl chloride, 165 g of 1-phenyl-2-methylamino-propanol-1 are boiled in 1000 cni3 of benzene for a few hours on a water bath.

   The phenylmethylaminopropanol which has separated out is filtered off, the benzene solution is neutralized with alcoholic hydrochloric acid and then filtered. The 1-phenyl-N-methyl-N-V-methogy-3'-methylbenzyl-2-aminopropanol-1-chlorohydrate obtained is recrystallized from alcohol. Melting point 207 to 209 '

      C. The yield is almost quantitative. The end product forms colorless crystals which are rather sparingly soluble in water and alcohol.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 1-Phenyl-N- methyl - N - 6'- methogy - 3'- methylbenzyl - 2- aminopropanol-l-chlorhydrat, dadurch ge kennzeichnet, @dass man 3-Methyl-6-methogy- benzylchlorid mit 1-Phenyl-2-methylamino- propanol-1 umsetzt. Das Endprodukt bildet farblose Kristalle, welche in Wasser und Alkohol ziemlich schwer löslich sind. PATENT CLAIM: Process for the production of 1-phenyl-N-methyl - N - 6'-methogy - 3'-methylbenzyl - 2-aminopropanol-1-chlorohydrate, characterized @that one is 3-methyl-6-methogy-benzyl chloride with 1-phenyl-2-methylaminopropanol-1. The end product forms colorless crystals which are rather sparingly soluble in water and alcohol.
CH186667D 1934-07-05 1935-06-29 Process for the preparation of 1-phenyl-N-methyl-N-6'-methoxy-3'-methyl-benzyl-2-aminopropanol-1-chlorohydrate. CH186667A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE186667X 1934-07-05

Publications (1)

Publication Number Publication Date
CH186667A true CH186667A (en) 1936-09-30

Family

ID=5720043

Family Applications (1)

Application Number Title Priority Date Filing Date
CH186667D CH186667A (en) 1934-07-05 1935-06-29 Process for the preparation of 1-phenyl-N-methyl-N-6'-methoxy-3'-methyl-benzyl-2-aminopropanol-1-chlorohydrate.

Country Status (1)

Country Link
CH (1) CH186667A (en)

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