1,1'-Carbonyldiimidazole → HCID 14556122, compound

Participants

Reaction Steps

Tetrahydrofuran (50 ml) was added to a mixture of indole-5-carboxylic acid (2.42 g, 0.016 mole) and 1,1'-carbonyldiimidazole (2.43 g, 0.015 mole). The mixture was stirred for 1 hr while nitrogen was bubbled through the solution to remove the carbon dioxide that was evolved. Then 3-aminoquinuclidine (1.89 g, 0.015 mole) was added in one portion, and the mixture was stirred for 60 hr at room temperature. The solid product was collected by filtration to yield 3.75 g (86.8%). Recrystallization from methanol-isopropyl ether (with chilling) gave 1.89 g of the product as an off-white solid; m.p. 293°-295° C. The solid was vacuum dried at 82° C. for 16 hr, m.p. 293°-295° C.

Provenance & Evidence