Formaldehyde → HCID 178516429, compound

HRID 352299Notes

Reaction equation

HRID 352299 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]=[C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][C:16]3=[O:24])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH2:25]=O.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>CCO>[N:4]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]=[C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]([CH2:25][N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[C:16]3=[O:24])=[CH:9][CH:8]=2)[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 178517090HCID 178517090, compound

Product 1

HCID 178516429HCID 178516429, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-[(4-morpholinophenylamino)-methylene]-1,3-dihydro-indol-2-one (17.3 g, 53.8 mmol) and paraformaldehyde (2.43 g, 80.9 mmol.) in 125 mL of EtOH was treated with piperidine (5.87 mL, 59.3 mmol). The reaction mixture was then heated at a reflux temperature for 5 hours during which time a yellow precipitate formed. The reaction mixture was allowed to cool to room temperature and the solid was collected by filtration and washed with EtOH and dried under vacuum to give the title compound (21.5 g, 95%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was then heated at a reflux temperature for 5 hours during which time a yellow precipitate
  2. customformed
  3. filtrationthe solid was collected by filtration
  4. washwashed with EtOH
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f9941ee157e5427db0f760b6b0268f0d
Source dataset
uspto-grants-2004_06
Patent number
US06747025B1

Reaction notes

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