HCID 90417653, compound → HCID 68798350, compound

HRID 588275Notes

Reaction equation

HRID 588275 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[CH:8]=2)[NH:3]1>C(O)(C(F)(F)F)=O>[NH:14]1[CH2:13][CH2:12][CH:11]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C:2](=[O:1])[CH2:10]3)[CH2:16][CH2:15]1

Participants

3

Reactant 1

HCID 90417653HCID 90417653, compound

Product 1

HCID 68798350HCID 68798350, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of TFA (10 ml) was added tert-butyl 4-(2-oxoindolin-5-yl)piperidine-1-carboxylate (789 mg, 2.49 mmol) and stirred at room temperature for 30 min. The reaction mixture was concentrated. The residue was diluted with 1N HCl and extracted with CHCl3. The aqueous layer was added with 28% NH3 aq until pH 8 and extracted with CHCl3/EtOH (3/1). The organic layer was dried over Na2SO4 and concentrated to give 5-(piperidin-4-yl)indolin-2-one (409 mg, 76%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was diluted with 1N HCl
  3. extractionextracted with CHCl3
  4. additionThe aqueous layer was added with 28% NH3 aq until pH 8
  5. extractionextracted with CHCl3/EtOH (3/1)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e8abb2650fb24df98ceeda7586ad2446
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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