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Preparation of 5-Amino-1,2-dihydro-4-(1-methyl-4-piperidinyl)pyrrol-3-ones

Heterocycles , 2009, 78 (8), 2021-2032

DOI: 10.3987/COM-09-11701

Chalyk B. A.; Tverdokhlebov A. V.; Iminov R. T.; Tolmachev A. A.

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 (1). Cyclization of 1 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 quant. yields.

Chalyk B. A.; Tverdokhlebov A. V.; Iminov R. T.; Tolmachev A. A.
Heterocycles 2009, 78 (8), 2021-2032
DOI: 10.3987/COM-09-11701

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