Formaldehyde → HCID 71278947, compound

HRID 1749765Notes

Reaction equation

HRID 1749765 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[CH2:19]=O>C(O)C>[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 531671-MethylpiperazineHCID 2357176-Hydroxy-3-coumaranone

Product 1

HCID 71278947HCID 71278947, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-hydroxybenzofuran-3(2H)-one (2.00 g, 13.3 mmol) in ethanol (25 mL) was added with N-methylpiperazine (1.33 g, 13.3 mmol), and 37% aqueous formaldehyde (1.08 g, 13.3 mmol) at room temperature. The mixture was stirred overnight at room temperature, and then subjected to suction filtration, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 6-hydroxy-7-[(4-methylpiperazin-1-yl)methyl]benzofuran-3(2H)-one (1.87 g, 54%).

Workup

  1. filtrationsubjected to suction filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-7272216a2566470994116bab327b5abb
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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