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A solution of indole-6-carboxylic acid (9.41 g) and 1,1'carbonyldiimidazole (10.6 g) in methylene chloride (290 ml) was heated at reflux, under nitrogen, for 30 minutes. The solution was cooled and treated with cyclopentylmethylamine (7.0 g). This mixture was heated to reflux for 30 minutes. The resultant solution was then diluted with methylene chloride, washed successively with 10% (v/v) hydrochloric acid, 20% (w/v) aqueous sodium hydroxide, and brine, dried (MgSO4), and evaporated to give 6-(N-cyclopentylmethylcarbamoyl)indole (14.4 g, 91%) as an ivory powder, mp 148°-150°; NMR (80 MHz, DMSO-d6): 3.19(dd, 2H, CH2NH), 6.46(br d, 1H, H3 -indole), 7.91(d, 1H, H7 -indole), 8.29(t, 1H, CH2NH).

1. temperatureat reflux, under nitrogen, for 30 minutes
2. temperatureThe solution was cooled
3. temperatureThis mixture was heated
4. temperatureto reflux for 30 minutes
5. washwashed successively with 10% (v/v) hydrochloric acid, 20% (w/v) aqueous sodium hydroxide, and brine
6. dry with materialdried (MgSO4)
7. customevaporated