Process for the preparation of dronedarone

Details Process for the preparation of dronedarone Process for the preparation of dronedarone

2007-12-25

2007-12-25

Dentz, Bernard (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S468000, C549S471000, C560S029000, C564S219000

Reexamination Certificate

active

10494960

ABSTRACT:
The present invention provides, according to an aspect thereof, a novel process for the preparation of dronedarone [1] and pharmaceutically acceptable salts thereof. According to a preferred embodiment, the process comprises N-acetylating of p-anisidine or p-phenetidine with acetic anhydride, reacting of the obtained N-(4-alkoxyphenyl)acetamide with 2-bromohexanoyl chloride or bromide in the presence of aluminum chloride or bromide to obtain N-[3-(2-bromohexanoyl)-4-hydroxyphenyl]acetamide [6a], converting the compound [6a] into 2-butyl-5-benzofuranamine hydrochloride [12a] and subsequently converting [12a] into [1] or pharmaceutically acceptable salts thereof. In accordance with another aspect of this invention, there are provided novel intermediates, inter alia the novel compounds [6a] and [12a]. The novel intermediates of the present invention are stable, solid compounds, obtainable in high yields, which can be easily purified by crystallization and stored for long periods of time.

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Horton, H. R. et al “Reactions with Reactive Alkyl Halides” Methods in Enzymology, vol. 11 (1967) pp. 556-565.
Raval, A. A. et al “Studies in Chalcones and Related Compounds Derived from 2-Hydroxy-5-acetaminoacetophenone:Part I. Synthesis of 2-Hydroxy-5′-acetaminochalcones and 6-Aminoflavones” J. Org. Chem., 21, (Dec. 1956) pp. 1408-1411.

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