tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-[(3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate

HRID 1749835Notes

Reaction equation

HRID 1749835 reaction equation
Br[CH2:2][C:3]1[C:11]2[O:10][CH2:9][C:8](=[O:12])[C:7]=2[CH:6]=[CH:5][CH:4]=1.C([O-])(=O)C.[Na+].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl>[O:12]=[C:8]1[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][N:28]3[CH2:27][CH2:26][N:25]([C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[CH2:30][CH2:29]3)[C:11]=2[O:10][CH2:9]1

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 517045Sodium AcetateHCID 601557897-bromomethylbenzofuran-3(2H)-one

Product 1

HCID 60155978Tert-butyl 4-[(3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylateYield 46.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-bromomethylbenzofuran-3(2H)-one (0.573 g, 2.52 mmol) in methylene chloride (20 mL) was added with sodium acetate (0.412 g, 5.03 mmol) and 1-tert-butoxycarbonylpiperazine (0.721 g, 3.87 mmol), and the mixture was stirred at room temperature for 6 hours. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl 4-[(3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.391 g, 46%).

Workup

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bbbbb9738c654ca0bfbd127dd63811fd
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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