Isatin → HCID 21699696, compound

HRID 1597276Notes

Reaction equation

HRID 1597276 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].C(O[N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][C:18]1=C=O)(C)(C)C.[C:26]([O-:29])(=[O:28])C.[NH4+:30]>CN(C)C=O>[C:6]([O:29][C:26]([N:17]1[CH2:18][CH2:19][C:20]2[N:1]=[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]3=[C:4]([C:2]([NH2:30])=[O:3])[C:21]=2[CH2:22]1)=[O:28])([CH3:11])([CH3:7])[CH3:4]

Participants

5

Reactant 3

HCID 7054IsatinHCID 517165Ammonium AcetateHCID 86757431HCID 86757431, compound

Product 1

HCID 21699696HCID 21699696, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isatin (3.99 g, 20 mmol) and 1-t-butoxy-carbonyl-4-piperidone (2.94 g, 20 mmol) were dissolved in N,N-dimethylformamide (20 ml), followed by adding thereto ammonium acetate (4.63 g, 60 mmol), and the resulting mixture was stirred at 120° C. for 3 hours. The solvent was removed by concentration under reduced pressure, and acetone (20 ml) and water (20 ml) were added to the residue. The resulting slurry was filtered and the solid thus obtained was purified by suspension in ethyl acetate/hexane to obtain the desired compound (3.34 g, 50%) as a light-brownish-white solid.

Workup

  1. additionby adding
  2. customThe solvent was removed by concentration under reduced pressure, and acetone (20 ml) and water (20 ml)
  3. additionwere added to the residue
  4. filtrationThe resulting slurry was filtered
  5. customthe solid thus obtained
  6. customwas purified by suspension in ethyl acetate/hexane

Sources & evidence

ORD record
ord-4b2fa69dfe73420b9c1079edf7a4a4f4
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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