Morpholine → HCID 21717309, compound

HRID 1386314Notes

Reaction equation

HRID 1386314 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.Cl[CH2:14][C:15]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[CH2:20]2)=[O:16]>CN(C=O)C.[I-].[K+]>[O:10]1[CH2:11][CH2:12][N:7]([CH2:14][C:15]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21](=[O:26])[CH2:20]3)=[O:16])[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 21717309HCID 21717309, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (800 mg, 5.8 mmol) followed by potassium iodide (30 mg, 0.2 mmol) and morpholine (500 μl, 5.7 mmol) were added to a solution of 5-(2-chloroacetyl)oxindole (1.05 g, 5 mmol), (J. Med. Chem. 1991, 1860), in DMF (20 ml) and the mixture was stirred for 1 hour at ambient temperature. The solvent was removed by evaporation and the residue was purified by reverse phase column chromatography on a Diaion (trade mark of Mitsubishi) HP20SS resin column, eluting with water/methanol (a gradient from 100/0 to 30/70). The purified product was then purified by chromatography on silica eluting with methylene chloride/methanol (95/5) to give 5-(2-morpholinoacetyl)oxindole (673 mg, 51%).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was purified by reverse phase column chromatography on a Diaion (trade mark of Mitsubishi) HP20SS resin column
  3. washeluting with water/methanol (a gradient from 100/0 to 30/70)
  4. customThe purified product was then purified by chromatography on silica eluting with methylene chloride/methanol (95/5)

Sources & evidence

ORD record
ord-8ec4c439d98a42dabd8e2f5a22ece28f
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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