Formaldehyde → HCID 86681959, compound

HRID 1749763Notes

Reaction equation

HRID 1749763 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2/[C:12](=[O:21])[C:13]3[C:18]([CH2:19]/2)=[CH:17][C:16]([OH:20])=[CH:15][CH:14]=3)=[CH:2]1.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].[CH2:35]=O>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2/[C:12](=[O:21])[C:13]3[C:18]([CH2:19]/2)=[C:17]([CH2:35][N:32]2[CH2:33][CH2:34][N:29]([C:27]([O:26][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:28])[CH2:30][CH2:31]2)[C:16]([OH:20])=[CH:15][CH:14]=3)=[CH:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 143452tert-Butyl piperazine-1-carboxylateHCID 71278900HCID 71278900, compound

Product 1

HCID 86681959HCID 86681959, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of (E)-2-[(1H-indol-3-yl)methylene]-5-hydroxy-2,3-dihydro-1H-inden-1-one (0.060 g, 0.22 mmol) in ethanol (3.0 mL) was added with 1-tert-butoxycarbonylpiperazine (0.049 g, 0.26 mmol), and 37% aqueous formaldehyde (0.020 g, 0.26 mmol), and the mixture was stirred overnight at 60° C. in a sealed tube. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain tert-butyl (E)-4-({2-[(1H-indol-3-yl)methylene]-5-hydroxy-1-oxo-2,3-dihydro-1H-inden-4-yl}methyl)piperazine-1-carboxylate (0.068 g, 65%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10))

Sources & evidence

ORD record
ord-b83eb2d497d24fa8a671e770906a03d7
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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