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

HRID 330140Notes

Reaction equation

HRID 330140 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][C:11]([OH:13])=O)[CH:8]=2)[CH:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:26]1([CH2:31][NH2:32])[CH2:30][CH2:29][CH2:28][CH2:27]1>C(Cl)Cl.CN(C)C=O>[CH:26]1([CH2:31][NH:32][C:11](=[O:13])[CH2:10][C:7]2[CH:8]=[C:9]3[C:4]([CH:3]=[CH:2][NH:1]3)=[CH:5][CH:6]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 80153CyclopentanemethylamineHCID 148825031H-Indole-6-acetic acid

Product 1

HCID 14882504N-cyclopentylmethylindole-6-acetamideYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

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).

Workup

  1. temperatureat reflux for 20 min
  2. temperatureheated
  3. temperatureat reflux for an additional 3 hr
  4. washwashed successively with 10% v/v hydrochloric acid, water and brine
  5. dry with materialdried (MgSO4)
  6. customand evaporated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 1:19 ethyl acetate

Sources & evidence

ORD record
ord-5c9ebd1e429c49cd9c02a3ec3d935cd7
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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