Water → HCID 10198779, compound

HRID 24381Notes

Reaction equation

HRID 24381 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[N:14]1([CH2:2][CH2:3][C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8](=[O:13])[CH2:7]3)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 145813925-(2-Chloroethyl)Oxindole

Product 1

HCID 10198779HCID 10198779, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-(2-chloroethyl)-2-oxindole (2.3 g), morpholine (1.2 ml) and diisopropylethylamine (1.2 ml) in dimethylsulfoxide (10 ml) was heated overnight at 100° C. The mixture was cooled, poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried and evaporated. The residue was chromatographed (silica gel, 5% methanol in chloroform) to give 0.9 g (31%) of 5-(2-morpholin-4-yl-ethyl)-2-oxindole as a white solid.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed (silica gel, 5% methanol in chloroform)

Sources & evidence

ORD record
ord-67f2ff75860a4699856618a7b3ffd152
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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