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

HRID 47247Notes

Reaction equation

HRID 47247 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-d6d1ad98c2dc4060a057b4e3d87c0662
Source dataset
uspto-grants-2004_03
Patent number
US06699863B1

Reaction notes

Loading…