Process for making galantamine

Details Process for making galantamine Process for making galantamine

2011-07-26

2011-07-26

Kumar, Shailendra (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C564S138000, C540S576000

Reexamination Certificate

active

07985879

ABSTRACT:
A novel process for the preparation of N-methyl-N-(2-[4-hydroxyphenyl]ethyl)-5-hydroxy-4-methoxy benzene carboxamide, which is useful as an intermediate in the synthesis of (−)-galantamine, comprises the reaction of a 5-hydroxy-4-methoxy benzoic acid derivative with N-methyl-N-(2-[4-hydroxyphenyl]ethyl) amine.

REFERENCES:
patent: WO 96/40751 (1996-12-01), None
Marco-Contelles, et al., Synthesis and Pharmacology of Galantamine,Chem. Rev. 2006, 106, 116-133.
T. Kametani, et al., Studies on the Synthesis of heterocyclic Compounds. Part CCCXV. Modified Total Synthesis of (±)-Galanthamine through Phenol Oxidation, J. Chem. Soc. (C), p. 2603-2605, 1969.
T. Kametani, et al., Modified Total Synthesis of (±)-Galanthamine through Phenol Oxidation,Chemical Communications, 1969, p. 425-426.
T. Kametani, et al., Studies of Synthesis of Heterocyclic Compounds. Part DVII(1). A Synthesis of (±)-N-Norgalanthamine, Feb. 1973, p. 35-37.
Marco et al., Galanthamine, a Natural Product for the Treatment of Alzheimer's Disease,Recent Patents on CNS Drug Discovery2006, 1(1):105-111.
Montalbetti et al., Amid Bond Formation and Peptide Coupling,Tetrahedron2005, 61:10827-10852-10852.

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