Formaldehyde → HCID 60155788, compound

HRID 1749708Notes

Reaction equation

HRID 1749708 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\[O:12][C:13]3[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[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\[O:12][C:13]3[C:20]([CH2:35][N:32]4[CH2:33][CH2:34][N:29]([C:27]([O:26][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:28])[CH2:30][CH2:31]4)=[C:19]([OH:21])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 143452tert-Butyl piperazine-1-carboxylateHCID 1777704HCID 1777704, compound

Product 1

HCID 60155788HCID 60155788, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (0.20 g, 0.72 mmol) obtained in Example A1, Step 1 in ethanol (10 mL) was added with 1-tert-butoxycarbonylpiperazine (0.16 g, 0.87 mmol), and 37% aqueous formaldehyde (0.068 g, 0.87 mmol), and the mixture was stirred overnight at 80° C. in a sealed tube. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (90:10)) to obtain tert-butyl (Z)-4-({2-[(1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.22 g, 63%).

Workup

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

Sources & evidence

ORD record
ord-57fb9526ce694ec38806b49866c6a98a
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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