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

HRID 492164Notes

Reaction equation

HRID 492164 reaction equation
[C:1]1(=[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]2=[O:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][O:2]1.[CH2:20]=O.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CCO.O1CCOCC1>[C:1]1(=[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:20][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:11]2=[O:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][O:2]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 687793813-(2-Benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 688358013-(3H-Isobenzofuran-1-ylidene)-1-piperidin-1-ylmethyl-1,3-dihydro-indol-2-oneYield 62.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (4.32 g, 17.3 mmol), paraformaldehyde (0.99 g, 32.9 mmol), and piperidine (2.14 mL, 21.7 mmol) in 192 mL EtOH and 48 mL dioxane was heated at reflux for 18.5 h. The solution was concentrated in vacuo to a volume of 100 mL and then refluxed for 1 h to dissolve the precipitant. The mixture was allowed to cool to room temperature and the precipitate filtered to give the title compound (3.728 g) as a bright yellow solid. An additional 0.52 g of the title compound was obtained by crystallization of the filtrate from ethyl acetate. The two lots were combined to give 4.248 g (71%) of the title compound as a bright yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18.5 h
  3. concentrationThe solution was concentrated in vacuo to a volume of 100 mL
  4. temperaturerefluxed for 1 h
  5. dissolutionto dissolve the precipitant
  6. filtrationthe precipitate filtered

Sources & evidence

ORD record
ord-cb21ffbde07e4a28933cd7b944cbaf3c
Source dataset
uspto-grants-2009_05
Patent number
US07531665B2

Reaction notes

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