Formaldehyde → HCID 71278788, compound

HRID 1749698Notes

Reaction equation

HRID 1749698 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.[CH3:22][O:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[CH2:32]=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]([CH2:32][N:29]4[CH2:30][CH2:31][N:26]([CH2:25][CH2:24][O:23][CH3:22])[CH2:27][CH2:28]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 1777704HCID 1777704, compoundHCID 27346381-(2-Methoxyethyl)piperazine

Product 1

HCID 71278788HCID 71278788, compoundYield 33%

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 (0.051 g, 0.19 mmol) obtained in Example A1, Step 1 in ethanol (2.0 mL) was added with 1-(2-methoxyethyl)piperazine (0.036 g, 0.25 mmol), and 37% aqueous formaldehyde (0.021 g, 0.25 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 (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxy-7-{[4-(2-methoxyethyl)piperazin-1-yl]methyl}benzofuran-3(2H)-one (0.027 g, 33%).

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-bd6b3b3b196644ae857fb9922d962947
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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