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

HRID 1749937
Notes
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Reaction equation

HRID 1749937 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 sodium chloride, 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 sodium chloride
  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-1762d13f225144f3b53de9d133a588d5
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09156827B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes