1,1'-Carbonyldiimidazole → 6-(N-cyclopentylmethylcarbamoyl)indole

HRID 1198956Notes

Reaction equation

HRID 1198956 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=2)[CH:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:25]1([CH2:30][NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26]1>C(Cl)Cl>[CH:25]1([CH2:30][NH:31][C:10]([C:7]2[CH:8]=[C:9]3[C:4]([CH:3]=[CH:2][NH:1]3)=[CH:5][CH:6]=2)=[O:12])[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 80153CyclopentanemethylamineHCID 5952301H-indole-6-carboxylic acid

Product 1

HCID 149485056-(N-cyclopentylmethylcarbamoyl)indoleYield 101.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d63396f115ec4974845a8474a041a488
Source dataset
uspto-grants-1990_02
Patent number
US04898863

Reaction notes

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