Formaldehyde → HCID 86681922, compound

HRID 1749727Notes

Reaction equation

HRID 1749727 reaction equation
[OH:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6](=[O:20])/[C:7](=[CH:9]/[C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][C:11]=3[CH3:19])/[O:8][C:4]=2[CH:3]=1.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].[CH2:36]=O>CO>[OH:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6](=[O:20])/[C:7](=[CH:9]/[C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][C:11]=3[CH3:19])/[O:8][C:4]=2[C:3]=1[CH2:36][N:33]1[CH2:34][CH2:35][N:30]([C:28]([O:27][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:29])[CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 143452tert-Butyl piperazine-1-carboxylateHCID 71278696HCID 71278696, compound

Product 1

HCID 86681922HCID 86681922, compoundYield 284.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of (Z)-6-hydroxy-2-[(2-methyl-1H-indol-3-yl)methylene]benzofuran-3(2H)-one (0.052 g, 0.18 mmol) in methanol (3.0 mL) was added with 1-tert-butoxycarbonylpiperazine (0.040 g, 0.23 mmol), and 37% aqueous formaldehyde (0.019 g, 0.023 mmol), and the mixture was stirred overnight at 70° 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 (95:5)) to obtain tert-butyl (Z)-4-({6-hydroxy-2-[(2-methyl-1H-indol-3-yl)methylene]-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.032 g, 36%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (95:5))

Sources & evidence

ORD record
ord-2791e49ec71c4265ae87e7c1c4f1f87f
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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