Triethylamine → 4-(3-Indolyl)-1-[(4-oxo-3-thiazolidinyl)acetyl]piperidine

Participants

Reaction Steps

A solution of 4-oxo-3-thiazolidinylacetyl chloride (1.75 g) in tetrahydrofuran (5.00 ml) was added dropsise to a suspension of 3-(4-piperidyl)indole (2.00 g) and triethylamine (4.10 ml) in a mixture of tetrahydrofuran (15.0 ml) and chloroform (5.00 ml) at 4° to 7° C. with stirring. After the mixture was allowed to stir for 1 hour with ice-bath cooling, the resultant precipitate was removed by filtration and the solvent was evaporated in vacuo. The residue was mixed with saturated aqueous sodium hydrogen carbonate (10.0 ml) and the mixture was extracted with chloroform (20.0 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of methanol and acetone to give 4-(3-indolyl)-1-[(4-oxo-3-thiazolidinyl)acetyl]piperidine (0.92 g) as slightly brown prisms.

Provenance & Evidence