Reaction #417322

Reaction equation

indole-6-acetic acid

1,1'-carbonyldiimidazole

cyclopentylmethylamine

→

N-cyclopentylmethylindole-6-acetamide

Yield 81.0%

Solvents

methylene chloride

methylene chloride

N,N-dimethylformamide

Conditions

Workup

1. 1
   Temperatureat reflux for 20 min
2. 2
   Temperatureheated
3. 3
   Temperatureat reflux for an additional 3 hr
4. 4
   Washwashed successively with 10% v/v hydrochloric acid, water and brine
5. 5
   Dryingdried (MgSO4)
6. 6
   Otherand evaporated
7. 7
   OtherThe residue was purified by flash chromatography
8. 8
   Washeluting with 1:19 ethyl acetate

Procedure

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).

Source