DE527620C - Process for the preparation of optically active phenylpropanolmethylamine - Google Patents

Process for the preparation of optically active phenylpropanolmethylamine

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Publication number
DE527620C
DE527620C DEI35388D DEI0035388D DE527620C DE 527620 C DE527620 C DE 527620C DE I35388 D DEI35388 D DE I35388D DE I0035388 D DEI0035388 D DE I0035388D DE 527620 C DE527620 C DE 527620C
Authority
DE
Germany
Prior art keywords
phenylpropanolmethylamine
optically active
preparation
phenylpropanolmethylbenzylamine
tartaric acid
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
DEI35388D
Other languages
German (de)
Inventor
Dr Franz Flaecher
Dr Friedrich Stolz
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 DEI35388D priority Critical patent/DE527620C/en
Application granted granted Critical
Publication of DE527620C publication Critical patent/DE527620C/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 aktivem Phenylpropanolmethylamin Die von Kanao (Seizo Kanao, Journ. pharm. Soc. Japan [=927], Nr. 540, S. 17 bis 23, referiert im Chemischen Zentralblatt 1927, i, S. 2538) und Nagai und Kanao (Liebigs Annalen, 47o, S. 165) durchgeführte Spaltung des racemischen Phenylpropanolmethylamins mit Hilfe von d-Weinsäure ist bekannt, liefert jedoch im Gegensatz zu den Angaben der genannten Veröffentlichungen nur unreines d-weinsaures 1-Phenylpropanolmethylamin, da es stets durch kleinere oder größere Mengen des d-Bitartrats der d,1-Base verunreinigt ist.Process for the preparation of optically active phenylpropanolmethylamine The Kanao (Seizo Kanao, Journ. Pharm. Soc. Japan [= 927], No. 540, pp. 17 bis 23, reported in Chemisches Zentralblatt 1927, i, p. 2538) and Nagai and Kanao (Liebigs Annalen, 47o, p. 165) carried out cleavage of the racemic phenylpropanolmethylamine with the help of d-tartaric acid is known, but provides contrary to the information of the publications mentioned only impure d-tartaric 1-phenylpropanolmethylamine, since it is always contaminated by smaller or larger amounts of the d-bitartrate of the d, 1-base is.

Es wurde nun gefunden, daß durch den Ersatz des Wasserstoffs am Stickstoff des d,1-Phenylpropanolmethylamins durch eine Aralkylgruppe der Löslichkeitsunterschied der d-Bitartrate von den d- und 1-Basen derartig gesteigert wird, daß dadurch eine quantitative Trennung der Racemverbindung in die rechts- und linksdrehende Form ermöglicht wird, und daß diese optisch aktiven Aralkylamine beim Hydrieren unter Abspaltung der Aralkylgruppe in die optisch aktiven Phenyhnethylpropanolamine übergeführt werden können. Beispiel 5009 Phenylpropanolmethylbenzylamin (F.72 bis 73°) werden mit einer Lösung von 295 g d-Weinsäure in 2 kg Wasser vermischt, worauf sich sofort das d-weinsaure d-Phenylpropanol= methylbenzylamin abscheidet. Durch Erwärmen und weiteren Zusatz von Wasser wird das Salz in Lösung gebracht. Nach einigen Stunden ist das d-weinsaure d-Phenylpropanolmethylbenzylamin auskristallisiert; nach ein- bis zweimaligem Umlösen aus Wasser schmilzt es bei zoz bis x02°. Aus der vereinigten Mutterlauge kristallisiert beim Stehen noch etwas d-weinsaures d-Phenylpropanolmethylbenzylamin aus, das abfiltriert wird.It has now been found that by replacing the hydrogen on the nitrogen of the d, 1-phenylpropanolmethylamine by an aralkyl group the difference in solubility of the d-bitartrate from the d- and 1-bases is increased in such a way that a quantitative separation of the racemic compound into the dextrorotatory and levorotatory form is made possible, and that these optically active aralkylamines upon hydrogenation with cleavage of the aralkyl group into the optical active Phenyhnethylpropanolamine can be converted. Example 5009 Phenylpropanolmethylbenzylamine (temperature 72 to 73 °) are mixed with a solution of 295 g of d-tartaric acid in 2 kg of water, whereupon the d-tartaric acid d-phenylpropanol = methylbenzylamine separates out immediately. The salt is dissolved by heating and adding more water. After a few hours, the d-tartaric acid d-phenylpropanolmethylbenzylamine has crystallized out; after being dissolved once or twice in water, it melts at zoz to x02 °. A little d-tartaric acid d-phenylpropanolmethylbenzylamine crystallizes out of the combined mother liquor on standing and is filtered off.

Im Filtrat befindet sich das d-weinsauer 1-Phenylpropanolmethylbenzylamin gelöst. Die daraus mittelsAlkaliabgeschiedeneBaseschmilzt nach dem Umkristallisieren aus Petroläther bei 49 bis 50°. Das 1-Phenylpropanolmethylbenzylamin wird entweder als salzsaures Salz in wäßriger Lösung oder als freie Base in alkoholischer Lösung katalytisch hydriert. Man erhält dann neben Toluol 1-Phenylpropanolmethylamin. Dieses kann über das Oxalat oder das Hydrochlorid gereinigt werden. Das salzsaure Salz schmilzt bei 215 bis 2i6°. Die spezifische Drehung des letzteren beträgt [oc] D = - 35°. Ausbeute 1844 g = g=,8 % der Theorie. Die aus dem salzsauren Salz abgeschiedene Base schmilzt bei 39 bis 4o°.The d-tartaric 1-phenylpropanolmethylbenzylamine is dissolved in the filtrate. The base deposited therefrom by means of alkali melts after recrystallization from petroleum ether at 49 to 50 °. 1-Phenylpropanolmethylbenzylamine is catalytically hydrogenated either as a hydrochloric acid salt in an aqueous solution or as a free base in an alcoholic solution. In addition to toluene, 1-phenylpropanolmethylamine is then obtained. This can be cleaned via the oxalate or the hydrochloride. The hydrochloric acid salt melts at 215 to 26 °. The specific rotation of the latter is [oc] D = - 35 °. Yield 1844 g = g = .8% of theory. The base separated from the hydrochloric acid salt melts at 39 to 40 °.

In gleicher Weise gewinnt man aus dem d-Phenylpropanolmethylbenzylamin (Ausbeute 246,2 g) durch katalytische Hydrierung das d-Phenylpropanohnethylamin mit dem Schmelzpunkt 39 bis 40°.In the same way, the d-phenylpropanolmethylbenzylamine (yield 246.2 g) is obtained by catalytic hydrogenation from the d-phenylpropanolmethylbenzylamine with a melting point of 39 ° to 40 °.

Das noch nicht beschriebene Phenylpropanolmethylbenzylamin wird aus Methylbenzylaminopropiophenon nach Patent 5247I7 mit Hilfe von geeigneten Reduktionsmitteln, z. B. Natrium und Alkohol, gewonnen oder durch Einwirkung von Benzylchlorid auf Phenylpropanolmethylamin. Es bildet farblose Kristalle, die bei 72 bis 73° schmelzen. Im Wasser ist es kaum löslich, in den meisten organischen Lösungsmitteln leicht löslich.The not yet described Phenylpropanolmethylbenzylamin is from Methylbenzylaminopropiophenone according to patent 5247I7 with the help of suitable reducing agents, z. B. sodium and alcohol, obtained or by the action of benzyl chloride Phenylpropanolmethylamine. It forms colorless crystals that melt at 72 to 73 °. It is hardly soluble in water and easily soluble in most organic solvents soluble.

Claims (1)

PATRNTANSPRUCH: Verfahren zur Darstellung von optisch aktivem Phenylpropanolmethylamin, darin bestehend, daß man synthetisches Phenylpropanolmethylaralkylamin mittels Weinsäure iri die optisch aktiven Komponenten spaltet und aus den optisch aktiven PhenylpropanolmethylaTalkylaminen durch Hydrieren die Aralkylgruppe abspaltet.PATENT CLAIM: Process for the preparation of optically active phenylpropanolmethylamine, consisting in that synthetic phenylpropanolmethylaralkylamine using tartaric acid iri splits the optically active components and from the optically active PhenylpropanolmethylaTalkylaminen splitting off the aralkyl group by hydrogenation.
DEI35388D 1928-09-04 1928-09-04 Process for the preparation of optically active phenylpropanolmethylamine Expired DE527620C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI35388D DE527620C (en) 1928-09-04 1928-09-04 Process for the preparation of optically active phenylpropanolmethylamine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI35388D DE527620C (en) 1928-09-04 1928-09-04 Process for the preparation of optically active phenylpropanolmethylamine

Publications (1)

Publication Number Publication Date
DE527620C true DE527620C (en) 1931-06-19

Family

ID=7188976

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI35388D Expired DE527620C (en) 1928-09-04 1928-09-04 Process for the preparation of optically active phenylpropanolmethylamine

Country Status (1)

Country Link
DE (1) DE527620C (en)

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