Sodium Iodide → HCID 16662377, compound

Participants

Reaction Steps

A mixture of 4-(chloromethyl)-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one a56 (0.26 g, 0.74 mmol, 1 eq), potassium carbonate (0.4 g, 2.96 mmol, 4 eq), 1-cyclopentylpiperazine a58 (0.34 g, 2.22 mmol, 3 eq) and a catalytic amount of sodium iodide in acetonitrile (20 ml) is stirred at reflux for 4 days. Potassium carbonate is filtered and the mixture is concentrated under vacuum, then the residue is dissolved in ethyl acetate, and washed twice with a saturated solution of aqueous sodium hydrogenocarbonate. The organic layer is dried over magnesium sulfate and concentrated under vacuum to give 0.17 g of crude material. This product is purified by chromatography over silicagel (dichloromethane/methanol/ammonia 94/6/0.6) to afford 0.052 g of 4-[(4-cyclopentylpiperazin-1-yl)methyl]-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one 44 as an orange oil.

Provenance & Evidence