One-pot process for the preparation of antiemetic agent,...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C548S300100

Reexamination Certificate

active

07547791

ABSTRACT:
A one-pot industrial process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazole-1-yl)methyl]-4H-carbazol-4-one of Formula-(I) from 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one of Formula-(IV) involves reaction of Formula (IV) with HNR1R2salt and paraformaldehyde, where R1,R2are independently alkyl groups or together forms a cyclic alkyl group, in a solvent system of acetic acid and hydrocarbon solvent to form a crude mixture of intermediate compounds of Formula (III) and (VIII), which is converted to ondansetron (Formula (I)) without isolation by reaction with 2methyimidazole in a suitable solvent system in the same pot.

REFERENCES:
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patent: 2002/0107275 (2002-08-01), Lidor-Hadas et al.
patent: 2004/0181076 (2004-09-01), Hesoun et al.
patent: 2004/0198794 (2004-10-01), Westheim et al.
Armarego, W.L.F.; Perrin, D.D. (1997). Purification of Laboratory Chemicals (4th Edition). Elsevier. Online version available at: www.knovel.com/knovel2/Toc.jsp?BookID=489&VerticalID=0.

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