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

HRID 492167Notes

Reaction equation

HRID 492167 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[C:12]1[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]1=[O:21])[O:7][CH2:6]2.[CH2:23]=O.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CCO>[CH3:1][N:2]([CH3:22])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[C:12]1[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:23][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:13]1=[O:21])[O:7][CH2:6]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 688381003-(5-Dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one

Product 1

HCID 688397743-(5-Dimethylamino-3H-isobenzofuran-1-ylidene)-1-piperidin-1-ylmethyl-1,3-dihydro-indol-2-oneYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(5-Dimethylamino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (550 mg, 1.88 mmol), paraformaldehyde (141 mg, 4.7 mmol) and piperidine (240 mg, 2.82 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 (655 mg, 89%) 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-bf997f6473764a1fb63b959b037519b8
Source dataset
uspto-grants-2009_05
Patent number
US07531665B2

Reaction notes

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