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Paper | Regular issue | Vol 78, No. 8, 2009, pp.2021-2032
Published online, 15th April, 2009
DOI: 10.3987/COM-09-11701
Preparation of 5-Amino-1,2-dihydro-4-(1-methyl-4-piperidinyl)pyrrol-3-ones

Bohdan A. Chalyk, Anton V. Tverdokhlebov,* Rustam T. Iminov, and Andrey A. Tolmachev

*Enamine Ltd. Co., Alexandra Matrosova Str. 23, 01103 Kiev, Ukraine


Acylation of (1-methyl-4(1H)-pyridinylidene)acetonitrile with chloroacetyl chloride was found to occur at the exocyclic carbon atom leading to 4-chloro-2-(1-methyl-4(1H)-pyridinylidene)-3-oxobutanenitrile. Its reaction with primary amines furnished 4-(2-amino-4,5-dihydro-4-oxo-1H-pyrrol-3-yl)- 1-methylpyridinium chlorides. Hydrogenation of these quaternary salts afforded 5-amino-1,2-dihydro-4-(1-methyl-4-piperidinyl)-3H-pyrrol-3-ones in nearly quantitative yields.