PROCESS FOR THE PREPARATION OF 4-(4-AMINOPHENYL)MORPHOLIN-3-ONE

PROCESS FOR THE PREPARATION OF 4-(4-AMINOPHENYL)MORPHOLIN-3-ONE

The field of this invention relates to a novel process, suitable for industrial scale manufacture, for the preparation of 4-(4-aminophenyl)morpholin-3-one of Formula (I), the key intermediate of rivaroxaban according to the scheme. In the process 2-(2-chloroethoxy)ethanol of Formula (XI) is oxidized...

Ausführliche Beschreibung

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Bibliographische Detailangaben
Hauptverfasser: GARADNAY Sandor, SZABO Tamas, NEU Jozsef
Format: Patent
Sprache:eng ; slv
Schlagworte:
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Beschreibung
Zusammenfassung:The field of this invention relates to a novel process, suitable for industrial scale manufacture, for the preparation of 4-(4-aminophenyl)morpholin-3-one of Formula (I), the key intermediate of rivaroxaban according to the scheme. In the process 2-(2-chloroethoxy)ethanol of Formula (XI) is oxidized to 2-(2-chloroethoxy)- acetic acid with aqueous sodium- or calcium-hypochlorite and a catalyst. The 2-(2~ chloroethoxy)acetic acid of Formula (X) is reacted with 4-nitro-aniline of Formula (VII) with phenylboronic acid catalyst. Then the 2-(2-chloroetoxy)-N-(4-nitrophenyl)acetamide of Formula (IX) is transformed to 4-(4-nitrophenyl)morpholin-3-one of Formula (IV) in a ,,one- pot" procedure. The 4-(4-nitrophenyl)morpholin-3-one of Formula (IV) is hydrogenated to get 4-(4-aminophenyl)morpholin-3-one of Formula (I).