Formaldehyde → 5-Chloro-3-(5-dimethylamino-3H-isobenzofuran-1-ylidene)-1-piperidin-1-ylmethyl-1,3-dihydro-indol-2-one

HRID 492169Notes

Reaction equation

HRID 492169 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]1[C:20]2[C:15](=[CH:16][C:17]([N:21]([CH3:23])[CH3:22])=[CH:18][CH:19]=2)[CH2:14][O:13]1.[CH2:24]=O.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CCO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:24][N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:6](=[O:11])[C:5]2=[C:12]1[C:20]2[C:15](=[CH:16][C:17]([N:21]([CH3:23])[CH3:22])=[CH:18][CH:19]=2)[CH2:14][O:13]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 688358045-Chloro-3-(5-dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydroindol-2-one

Product 1

HCID 688347925-Chloro-3-(5-dimethylamino-3H-isobenzofuran-1-ylidene)-1-piperidin-1-ylmethyl-1,3-dihydro-indol-2-oneYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-Chloro-3-(5-dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (400 mg, 1.22 mmol), paraformaldehyde (91 mg, 3.05 mmol) and piperidine (156 mg, 1.83 mmol) in 20 mL of EtOH was stirred at reflux for overnight and cooled to room temperature. The solid which formed on cooling was collected by filtration, washed with EtOH (5 mL) and dried under vacuum to give the title compound (500 mg, 97%) as bright yellow crystals.

Workup

  1. temperatureat reflux for overnight
  2. customThe solid which formed
  3. temperatureon cooling
  4. filtrationwas collected by filtration
  5. washwashed with EtOH (5 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-8f54b5f45cc945879eccf78aa7042507
Source dataset
uspto-grants-2009_05
Patent number
US07531665B2

Reaction notes

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