Chloroacetamide → 2-(2,3,3a,8b-Tetrahydrocyclopenta[b]Indol-4(1H)-yl)Acetamide

HRID 898746Notes

Reaction equation

HRID 898746 reaction equation
[CH2:1]1[CH:12]2[CH:4]([NH:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=32)[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.Cl[CH2:23][C:24]([NH2:26])=[O:25]>CN(C=O)C>[CH2:1]1[CH:12]2[CH:4]([N:5]([CH2:23][C:24]([NH2:26])=[O:25])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=32)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 81531DiisopropylethylamineHCID 218735741,2,3,3a,4,8b-Hexahydrocyclopenta[b]indole

Product 1

HCID 218735702-(2,3,3a,8b-Tetrahydrocyclopenta[b]Indol-4(1H)-yl)AcetamideYield 69.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole (130 mmol, 21 g) in DMF (50 mL) was added diisopropylethylamine (400 mmol, 70 mL) followed by 2-chloroacetamide (270 mmol, 25 g). The reaction mixture was heated to 100° C. for 18 h. The reaction was concentrated and the diluted with ethyl acetate and water. The phases were separated and the organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by flash column chromatography through silica gel (elution with 60% ethyl acetate-hexanes) to afford a yellow solid (90 mmol, 20 g, 69%).

Workup

  1. concentrationThe reaction was concentrated
  2. additionthe diluted with ethyl acetate and water
  3. customThe phases were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by flash column chromatography through silica gel (elution with 60% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-d0d512a9873d4d34a92e82bd3fb6a36d
Source dataset
uspto-grants-2008_04
Patent number
US07351839B2

Reaction notes

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