1,1'-Carbonyldiimidazole → N-cyclopentylmethylindole-6-acetamide

Participants

Reaction Steps

A solution of indole-6-acetic acid (0.70 g) and 1,1'-carbonyldiimidazole (0.83 g) in methylene chloride (20 ml) and N,N-dimethylformamide (5 ml) was heated at reflux for 20 min, treated with cyclopentylmethylamine (0.59 g), and heated at reflux for an additional 3 hr. The solution was diluted with methylene chloride; washed successively with 10% v/v hydrochloric acid, water and brine; dried (MgSO4); and evaporated. The residue was purified by flash chromatography, eluting with 1:19 ethyl acetate: hexane, to give N-cyclopentylmethylindole-6-acetamide (0.83, 81%) as a white powder; partial NMR (80 MHz, CDCl3): 3.13(t, 2H, NHCH2), 3.69(s, 2H, ArCH2), 6.55(m, 1H, H3 -indole), 6.98(dd, 1H, H5 -indole), 7.62(d, 1H, H4 -indole).

Provenance & Evidence