Piperidine → 3-methyl-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one

Participants

Reaction Conditions

Reaction Steps

5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 53f (30 mg, 0.09 mmol) and 6-methoxyl-1,3-dihydro-indol-2-one (13 mg, 0.08 mmol) were dissolved in 1560 of ethanol, and added with 4.4 μl of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred at 45° C. for 16 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled to room temperature, and filtered. The filter cake was washed with anhydrous ethanol (1 ml×2) and dried to obtain the title compound (R,Z)-5-(2-hydroxy-3-morpholinopropyl)-2-(6-methoxy-2-oxoindolin-3-ylidene) methyl)-3-methyl-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 77 (22 mg, yield 51%) as a yellow solid.

Provenance & Evidence