DE1044821B - Process for the production of 1-alkyl norharmanes (1-alkyl-3-carbolines) and their offshoots - Google Patents

Process for the production of 1-alkyl norharmanes (1-alkyl-3-carbolines) and their offshoots

Info

Publication number
DE1044821B
DE1044821B DEF22749A DEF0022749A DE1044821B DE 1044821 B DE1044821 B DE 1044821B DE F22749 A DEF22749 A DE F22749A DE F0022749 A DEF0022749 A DE F0022749A DE 1044821 B DE1044821 B DE 1044821B
Authority
DE
Germany
Prior art keywords
alkyl
carbolines
norharmanes
production
offshoots
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.)
Pending
Application number
DEF22749A
Other languages
German (de)
Inventor
Dr Helmut Timmler
Dr Rudolf Lorenz
Dr Hans Henecka
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Priority to DEF22749A priority Critical patent/DE1044821B/en
Publication of DE1044821B publication Critical patent/DE1044821B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Description

Verfahren zur Herstellung von 1-Alkylnorharmanen (1-Alkyl-3-carbolinen) und deren Abkömmlingen In der Hauptpatentanmeldung ist ein Verfahren zur Herstellung von Norharman (3-Carbolin) und seinen im Benzolkern durch Alkyl- oder Alkoxygruppen substituierten Abkömmlingen beschrieben. Das Verfahren besteht darin, daß man 2-Keto-2,3,4,5-tetrahydro-ß-carbolin oder dessen im Benzolkern substituierte Abkömmlinge mit Phosphoroxychlorid mindestens i/2 Stunde auf erhöhte Temperatur erhitzt.Process for the production of 1-alkyl norharmanes (1-alkyl-3-carbolines) and their descendants. In the main patent application is a method of manufacture from norharman (3-carboline) and its in the benzene nucleus through alkyl or alkoxy groups substituted descendants described. The method consists in that you 2-keto-2,3,4,5-tetrahydro-ß-carboline or its derivatives substituted in the benzene nucleus with phosphorus oxychloride at least Heated i / 2 hour at elevated temperature.

Es wurde nun gefunden, daß auch die 1-Alkyl-2-keto-2,3,4,5-tetrahydro-ß-carboline sowie ihre im Benzolkern durch Alkyl- oder Alkoxygruppen substituierten Abkömmlinge dieser Umsetzung zugänglich sind. Man erhält dann 1-Alkylnorharmane bzw. die entsprechenden Abkömmlinge.It has now been found that the 1-alkyl-2-keto-2,3,4,5-tetrahydro-ß-carbolines and their derivatives substituted by alkyl or alkoxy groups in the benzene nucleus are accessible to this implementation. Then 1-alkyl norharmanes or the corresponding ones are obtained Descendants.

Die Umsetzung wird so durchgeführt, daß man die Ausgangsstoffe mindestens i/2 Stunde mit Phosphoroxychlorid auf erhöhte Temperatur erhitzt.The reaction is carried out in such a way that the starting materials are at least Heated i / 2 hour with phosphorus oxychloride to elevated temperature.

Die Umsetzungsprodukte werden in guter Ausbeute und in kristalliner Form erhalten. Die 1-Alkylnorharmane werden als Zwischenprodukte für die Synthese pharmazeutisch wirksamer Verbindungen verwendet.The reaction products are obtained in good yield and in crystalline form. The 1-alkyl norharmanes are used as intermediates for the synthesis of pharmaceutically active compounds.

Beispiel 10 g 1-Methyl-2-keto-2,3,4,5-tetrahydro-ß-carbolin und 100 ccm Phosphoroxychlorid werden unter Rühren 2 Stunden gekocht. Die Lösung wird abgekühlt, auf Eiswasser gegossen und über Nacht stehengelassen. Man saugt danach die Mischung von einer geringen Menge nichtlöslicher Nebenprodukte ab und macht die Mutterlauge mit 10°/oiger Natronlauge alkalisch. Man nimmt die ausgefallene Verbindung in Chloroform auf, trocknet dieses und verdampft es. Das als Rückstand erhaltene 1-Methylnorharmanwirdallmählichkristallin;F.=109° C, aus Äther -Petroläther umkristallisiert; Ausbeute 5 g, entsprechend 55 % der Theorie; F. des Pikrates ist 258° C, F. des Hydrochlorids 290°C.Example 10 g of 1-methyl-2-keto-2,3,4,5-tetrahydro-β-carboline and 100 cc of phosphorus oxychloride are boiled for 2 hours with stirring. The solution is cooled, poured onto ice water and left to stand overnight. A small amount of insoluble by-products is then filtered off with suction from the mixture and the mother liquor is made alkaline with 10% strength sodium hydroxide solution. The precipitated compound is taken up in chloroform, dried and evaporated. The 1-methyl norharman obtained as residue gradually becomes crystalline; mp = 109 ° C, recrystallized from ether-petroleum ether; Yield 5 g, corresponding to 55 % of theory; The temperature of the picrate is 258 ° C, the temperature of the hydrochloride is 290 ° C.

Ausgehend vom 1-Methyl-2-keto-7-methoxy-2,3,4,5-tetrahydro-ß-carbolin erhält man in gleicher Weise das ölige 1-Methyl-7-methoxynorharman, dessen Hydrochlorid bei 262 bis 263°C schmilzt.Starting from 1-methyl-2-keto-7-methoxy-2,3,4,5-tetrahydro-β-carboline the oily 1-methyl-7-methoxynorharman and its hydrochloride are obtained in the same way melts at 262 to 263 ° C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 1-Alkylnorharmanen (1-Alkyl-3-carbolinen) und deren im Benzolkern durch Alkyl- oder Alkoxygruppen substituierten Abkömmlingen, dadurch gekennzeichnet, daß man in weiterer Ausbildung des Verfahrens der Patentanmeldung F 21404 IVb/12p 1-Alkyl-2-keto-2,3,4,5-tetrahydro-ßcarboline oder deren im Benzolkern durch Alkyl-oder Alkoxygruppen substituierte Abkömmlinge mit Phosphoroxychlorid mindestens '/,Stunde auf erhöhte Temperatur erhitzt.PATENT CLAIM: Process for the production of 1-alkyl norharmanes (1-alkyl-3-carbolines) and their derivatives substituted in the benzene nucleus by alkyl or alkoxy groups, characterized in that in a further development of the process of the patent application F 21404 IVb / 12p 1-alkyl-2-keto-2,3,4,5-tetrahydro-β-carbolines or their in the benzene nucleus by alkyl or alkoxy groups substituted derivatives with phosphorus oxychloride heated to an elevated temperature for at least half an hour.
DEF22749A 1957-04-05 1957-04-05 Process for the production of 1-alkyl norharmanes (1-alkyl-3-carbolines) and their offshoots Pending DE1044821B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF22749A DE1044821B (en) 1957-04-05 1957-04-05 Process for the production of 1-alkyl norharmanes (1-alkyl-3-carbolines) and their offshoots

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF22749A DE1044821B (en) 1957-04-05 1957-04-05 Process for the production of 1-alkyl norharmanes (1-alkyl-3-carbolines) and their offshoots

Publications (1)

Publication Number Publication Date
DE1044821B true DE1044821B (en) 1958-11-27

Family

ID=7090559

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF22749A Pending DE1044821B (en) 1957-04-05 1957-04-05 Process for the production of 1-alkyl norharmanes (1-alkyl-3-carbolines) and their offshoots

Country Status (1)

Country Link
DE (1) DE1044821B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1134221A1 (en) * 2000-03-15 2001-09-19 Aventis Pharma Deutschland GmbH Substituted beta-carbolines as lkB kinase inhibitors
WO2008104161A1 (en) * 2007-02-26 2008-09-04 Ellneuroxx Ltd. ß-CARBOLINES FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1134221A1 (en) * 2000-03-15 2001-09-19 Aventis Pharma Deutschland GmbH Substituted beta-carbolines as lkB kinase inhibitors
WO2008104161A1 (en) * 2007-02-26 2008-09-04 Ellneuroxx Ltd. ß-CARBOLINES FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
US8334299B2 (en) 2007-02-26 2012-12-18 Ellneuroxx, Ltd. β-carboline for the treatment of neurodegenerative diseases

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