DE599433C - Process for the preparation of optically levorotatory 1-phenyl-2-aminopropanol- (1) - Google Patents

Process for the preparation of optically levorotatory 1-phenyl-2-aminopropanol- (1)

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Publication number
DE599433C
DE599433C DEI45615D DEI0045615D DE599433C DE 599433 C DE599433 C DE 599433C DE I45615 D DEI45615 D DE I45615D DE I0045615 D DEI0045615 D DE I0045615D DE 599433 C DE599433 C DE 599433C
Authority
DE
Germany
Prior art keywords
levorotatory
optically
phenyl
aminopropanol
preparation
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEI45615D
Other languages
German (de)
Inventor
Dr Max Bockmuehl
Dr Gustav Ehrhart
Dr Leonhard Stein
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
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
Priority to DEI45615D priority Critical patent/DE599433C/en
Application granted granted Critical
Publication of DE599433C publication Critical patent/DE599433C/en
Expired legal-status Critical Current

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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
    • C07C215/22—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 unsaturated
    • C07C215/28—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 unsaturated and containing six-membered aromatic rings
    • C07C215/30—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 unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of 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 von optisch linksdrehenden 1-Phenyl-2-aminopropanolen-(1) Nach den bisher bekanntgewordenen Verfahren zur synthetischen Darstellung der als Heilmittel verwendeten linksdrehenden i-Phenyla-aminopropanole-(i) werden die Racemate der i-Phenyl-z-aminopropanole-(i) mit optisch aktiven Säuren gespalten.Process for the preparation of optically levorotatory 1-phenyl-2-aminopropanol- (1) According to the previously known method for the synthetic representation of the as Remedies used levorotatory i-phenyla-aminopropanols- (i) are the racemates the i-phenyl-z-aminopropanols- (i) cleaved with optically active acids.

Es wurde nun gefunden, daß man durch organische Synthese sofort zu den optisch linksdrehenden Aminoalkoholen gelangen kann, wenn man linksdrehendes i-Phenyla-ketopropanol- (i) in Gegenwart von Salzen des Ammoniaks oder primärer Alkyl- oder Aralkylamine mit Wasserstöff und Katalysatoren der Nickelgruppe behandelt.It has now been found that organic synthesis can be used immediately the optically levorotatory amino alcohols can get if one levorotatory i-Phenyla-ketopropanol- (i) in the presence of salts of ammonia or primary Treated alkyl or aralkylamines with hydrogen and nickel group catalysts.

Beispiele 1. 15 g 1-Phenylacetylcarbinol und '6,8 g Methylaminhydrochlorid werden in 25o ccm Alkohol gelöst und mit Nickel und Wasserstoff hydriert. Nach Aufnahme der berechneten Menge Wasserstoff saugt man vom Katalysator ab und dampft die alkoholische Lösung im Vakuum ein. Der erhaltene Rückstand wird in' wenig Wasser aufgenommen, mit festem Kaliumcarbonat versetzt und die abgeschiedene Base ausgeäthert. Nach dem Abdestillieren des Äthers wird das zurückbleibende Produkt mit alkoholischer Säure neutralisiert. Nach kurzer Zeit kristallisiert das 1-Phenylpropanolmethylaminhydrochlorid in guter Ausbeute aus, das nach dem Umkristallisieren aus absolutem Alkohol den Schmelzpunkt 216' zeigt.EXAMPLES 1. 15 g of 1-phenylacetylcarbinol and 6.8 g of methylamine hydrochloride are dissolved in 250 cc of alcohol and hydrogenated with nickel and hydrogen. After the calculated amount of hydrogen has been taken up, the catalyst is suctioned off and the alcoholic solution is evaporated in vacuo. The residue obtained is taken up in a little water, solid potassium carbonate is added and the base which has separated out is extracted with ether. After the ether has been distilled off, the remaining product is neutralized with alcoholic acid. After a short time, the 1-phenylpropanolmethylamine hydrochloride crystallizes out in good yield, which, after recrystallization from absolute alcohol, has a melting point of 216 ' .

z. 30 g 1-Phenylacetylcarbinol und i o, 5 g AmmoniumchIorid werden in zoo ccm 8o%igem Methylalkohol gelöst und mit Nilekel und Wasserstoff hydriert. Nach Beendigung der Wasserstoffaufnahme wird vom Methylalkohol abdestilliert, der Rückstand in Wasser aufgenommen, mit Kaliumcarbonat alkalisch gemacht und ausgeäthert. Benn Einleiten von gasförmiger Salzsäure in die trockene ätherische Lösung fällt das 1-Phenylpropanolaminhydrochlorid kristallinisch aus. Durch Umlösen aus Isopropylalkohol wird es von wenig anhaftendem racemischem Phenylpropanolaminhydrochlorid getrennt. Es schmilzt bei 174 bis 175° und hat eine spez. Drehung von 3. 30 g 1-Phenylacetylcarbinol werden mit einer Lösung von 21,4 g Benzylamin ,in 12 g Eisessig und azo ccm Alkohol versetzt und mit Nickel und Wasserstoff wie in Beispiel i hydriert. Die Aufarbeitung ergibt 1-Phenylpropanolbeiizylaminhydrochlorid vom Schmelzpunkt i g9 bis 20o° und einer spez. Drehung von z. 30 g of 1-phenylacetylcarbinol and 10.5 g of ammonium chloride are dissolved in zoo cc of 80% methyl alcohol and hydrogenated with Nilekel and hydrogen. After the uptake of hydrogen has ceased, the methyl alcohol is distilled off, the residue is taken up in water, made alkaline with potassium carbonate and extracted with ether. Benn introducing gaseous hydrochloric acid into the dry ethereal solution, the 1-phenylpropanolamine hydrochloride precipitates in crystalline form. It is separated from slightly adhering racemic phenylpropanolamine hydrochloride by redissolving it from isopropyl alcohol. It melts at 174 to 175 ° and has a spec. Rotation of 3. 30 g of 1-phenylacetylcarbinol are mixed with a solution of 21.4 g of benzylamine in 12 g of glacial acetic acid and azo cc alcohol and hydrogenated with nickel and hydrogen as in Example i. The work-up gives 1-Phenylpropanolbeiizylaminhydrochlorid from melting point i g9 to 20o ° and a spec. Rotation of

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von optisch linksdrehenden i - Fhenyl - z - aminopropanolen-(i ), dadurch gekennzeichnet, daPv man linksdrehendes i-Phenyl-z-ketopropanol-(i) in Gegenwart der Salze des Ammoniaks oder primärer Alkyl- oder Aralkylarrmine der Reduktion mit Wasserstoff und Katalysatoren der Nickelgruppe unterWir ft.PATENT CLAIM: Process for the representation of optically left-turning i - Fhenyl - z - aminopropanol- (i), characterized by the fact that one is left-handed i-Phenyl-z-ketopropanol- (i) in the presence of the salts of ammonia or primary alkyl or aralkyl arrays of reduction with hydrogen and catalysts of the nickel group unterWe ft.
DEI45615D 1930-09-19 1930-09-19 Process for the preparation of optically levorotatory 1-phenyl-2-aminopropanol- (1) Expired DE599433C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI45615D DE599433C (en) 1930-09-19 1930-09-19 Process for the preparation of optically levorotatory 1-phenyl-2-aminopropanol- (1)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI45615D DE599433C (en) 1930-09-19 1930-09-19 Process for the preparation of optically levorotatory 1-phenyl-2-aminopropanol- (1)

Publications (1)

Publication Number Publication Date
DE599433C true DE599433C (en) 1934-07-02

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEI45615D Expired DE599433C (en) 1930-09-19 1930-09-19 Process for the preparation of optically levorotatory 1-phenyl-2-aminopropanol- (1)

Country Status (1)

Country Link
DE (1) DE599433C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7414153B2 (en) 2004-04-15 2008-08-19 Emmellen Biotech Pharmaceuticals Limited Process for preparation of optically active 1-erythro-2-amino-1-phenyl-1-propanol

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7414153B2 (en) 2004-04-15 2008-08-19 Emmellen Biotech Pharmaceuticals Limited Process for preparation of optically active 1-erythro-2-amino-1-phenyl-1-propanol

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