N-bromobutanimide → Benzyl 4-(4-bromophenyl)piperazine-1-carboxylate

HRID 2403614Notes

Reaction equation

HRID 2403614 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:23]N1C(=O)CCC1=O>CN(C=O)C>[Br:23][C:4]1[CH:3]=[CH:2][C:1]([N:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:11][CH2:12]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 98792541-Piperazinecarboxylic acid, 4-phenyl-, phenylmethyl ester

Product 1

HCID 46739494Benzyl 4-(4-bromophenyl)piperazine-1-carboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl 4-phenylpiperazine-1-carboxylate (2.1 g) was dissolved in DMF (80 ml), and N-bromosuccinimide (1.4 g) was added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and subjected to liquid separation by the addition of CHCl3 and a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated and dried over Na2SO4, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain benzyl 4-(4-bromophenyl)piperazine-1-carboxylate (2.3 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customsubjected to liquid separation by the addition of CHCl3
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-566f931f23a84db8b2e1dbcdd053de75
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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