Piperidine → 3-Cyclopropylmethylene-1,3-dihydro-indol-2-one

HRID 74534Notes

Reaction equation

HRID 74534 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].N1[CH2:16][CH2:15][CH2:14][CH2:13]C1.C1(C=O)CC1>CO>[CH:15]1([CH:16]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 123114CyclopropanecarboxaldehydeHCID 321710Oxindole

Product 1

HCID 673385303-Cyclopropylmethylene-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.0 g (15 mmol) 1,3-dihydro-indol-2-one and 0.20 mL piperidine were placed in 20 mL methanol. 1.1 mL (15 mmol) cyclopropanecarboxaldehyde were added dropwise, the reaction mixture was refluxed for 3 h and then concentrated to dryness by rotary evaporation. The residue was triturated with diisopropylether and the solid remaining was suction filtered and dried.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 h
  2. concentrationconcentrated to dryness by rotary evaporation
  3. customThe residue was triturated with diisopropylether
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-bc1a2efd805141399f5afc4129d52659
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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