Diisopropylethylamine → 2-{3-[4-(3-Methylsulfanyl-phenyl)-piperazin-1-yl]-propoxy}-isoindole-1,3-dione

Participants

Reaction Steps

A solution prepared from N-(3-bromopropyloxy)phthalimide (5.00 g), 1-(3-methylthiophenyl)piperazine (3.85 g), diisopropylethylamine (4.55 g) and CH3CN (150 ml) was stirred at room temperature under N2 for 84 hr. The solution was concentrated in vacuo and dried under vacuum yielding 10.5 g of a foam. TLC analysis showed one major product. The foam was extracted with EtOAc (250 ml) yielding after concentration 7.1 g of an oil. The oil was chromatographed (2 silica gel columns) to provide 4.00 g of an oil. The oil was triturated with EtOAc/Et2O to give a solid which was recrystallized from EtOAc/Et2O yielding 3.08 g of crystals, mp 103°-106° C.

Provenance & Evidence