Phthalimide → 2-[(4-[(6-Chloro-2-naphthyl)sulfonyl]-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinyl)methyl]-1h-isoindole-1,3(2h)-dione

Participants

Reaction Conditions

Reaction Steps

A mixture of triphenylphosphine (0.49 g), phthalimide (0.29 g) and methylene chloride (15 ml) was combined with diethyl azodicarboxylate (0.29 ml) with stirring at 0° C., and stirred for 10 minutes. This solution was combined, at 0° C. with stirring, with a solution of 4-[(6-chloro-2-naphthyl)sulfonyl]-6-(hydoxymethyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-2-piperazinone hydrochloride (0.27 g) in methylene chloride (10 ml) and stirred at room temperature for 1 hour. The reaction mixture was washed with saturated aqueous sodium bicarbonate, dried, and concentrated under reduced pressure. The residue was purified by a column chromatography on a silica gel (dichloromethane: 10% aqueous ammonia-containing methanol=10:1) to obtain 2-[(4-[(6-chloro-2-naphthyl)sulfonyl]-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinyl)methyl]-1H-isoindole-1,3(2H)-dione (0.28 g) as a pale yellow powder.

Provenance & Evidence