Morpholine → HCID 18414718, compound

HRID 991838Notes

Reaction equation

HRID 991838 reaction equation
C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[C:34]([C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[NH:42][C:41](=[O:46])[CH2:40]2)([OH:36])=O.[NH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.C(N(CC)CC)C>ClCCl>[N:47]1([C:34]([C:37]2[CH:38]=[C:39]3[C:43](=[CH:44][CH:45]=2)[NH:42][C:41](=[O:46])[CH2:40]3)=[O:36])[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 2724699PyBOPHCID 27733182-Oxindole-5-carboxylic acid

Product 1

HCID 18414718HCID 18414718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

PyBOP (3.5 g, 6.72 mmol) was added to a mixture of 5-carboxy-2-oxindole (1 g, 5.6 mmol), morpholine (0.5 mL, 6.2 mmol) and triethylamine (2.0 mL, 14 mmol) in dichloromethane. After stirring at room temperature for 4 hours, the reaction was diluted with more dichloromethane, washed with saturated sodium bicarbonate and brine, dried and concentrated. The residue was purified by column chromatography to give 5-(morpholine-4-carbonyl)-1,3-dihydro-indol-2-one.

Workup

  1. washwashed with saturated sodium bicarbonate and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d1b7430726594d0a8449431236f9be67
Source dataset
uspto-grants-2002_10
Patent number
US06465507B2

Reaction notes

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