2-Morpholinoethylamine → 5-(2-Morpholinoethylaminosulphonyl)oxindole

HRID 1386330Notes

Reaction equation

HRID 1386330 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3].[NH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C(O)C>[O:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][NH:15][S:2]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)(=[O:4])=[O:3])[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 217173035-(2-Morpholinoethylaminosulphonyl)oxindoleYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 5-chlorosulphonyloxindole (1 g, 4.3 mmol), (prepared as described for the starting material in Example 60), and 4-(2-aminoethyl)morpholine (620 μl, 4.7 mmol) in ethanol (20 ml) was heated at 65° C. for 1 hour. The solvent was removed by evaporation, the residue was partitioned between methylene chloride and water and the aqueous layer was adjusted to pH7-8 with 5% aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 5-(2-morpholinoethylaminosulphonyl)oxindole (750 mg, 54%).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was partitioned between methylene chloride and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with methylene chloride/methanol (95/5)

Sources & evidence

ORD record
ord-e1fa01c8a58441a5acca466ca14cb5fd
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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