Formaldehyde → 7-[(cis-3,5-dimethylpiperazin-1-yl)methyl]-6-hydroxybenzofuran-3(2H)-one

HRID 1749851Notes

Reaction equation

HRID 1749851 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][C@H:13]1[NH:18][C@@H:17]([CH3:19])[CH2:16][NH:15][CH2:14]1.[CH2:20]=O>C(O)C>[CH3:19][C@H:17]1[NH:18][C@@H:13]([CH3:12])[CH2:14][N:15]([CH2:20][C:3]2[C:4]3[O:8][CH2:7][C:6](=[O:9])[C:5]=3[CH:10]=[CH:11][C:2]=2[OH:1])[CH2:16]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 2357176-Hydroxy-3-coumaranoneHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 712786977-[(cis-3,5-dimethylpiperazin-1-yl)methyl]-6-hydroxybenzofuran-3(2H)-oneYield 31.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-hydroxybenzofuran-3(2H)-one (0.300 g, 2.00 mmol) in ethanol (2 mL) was added with cis-3,5-dimethylpiperazine (0.288 g, 2.00 mmol), and 37% aqueous formaldehyde (0.162 g, 2.00 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature, and then concentrated. The resulting solid was dissolved in ethyl acetate, and the precipitated solid was removed by filtration. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain 7-[(cis-3,5-dimethylpiperazin-1-yl)methyl]-6-hydroxybenzofuran-3(2H)-one (0.173 g, 31%).

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting solid was dissolved in ethyl acetate
  3. customthe precipitated solid was removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4528504b84a640b5996ecf1f7b7a3f6b
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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