Dimethylformamide → 1-Benzyl-4-(2-nitrophenyl)piperazine

HRID 1242717Notes

Reaction equation

HRID 1242717 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].CCN(C(C)C)C(C)C.[CH2:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN(C=O)C>CCOC(C)=O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:30]1[CH2:31][CH2:32][N:27]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:28][CH2:29]1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 738951-Fluoro-2-nitrobenzeneHCID 759941-BenzylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 5181711-Benzyl-4-(2-nitrophenyl)piperazineYield 99.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 500 mL round-bottomed flask equipped with magnetic stirring was added 2-fluoronitrobenzene (14 g, 101 mmol), DIEA (19 mL, 110 mmol), 1-benzylpiperazine (18 mL, 110 mmol) (Aldrich) and DMF (250 mL). The reaction was stirred for 18 h, diluted with 400 mL of EtOAc and washed with 300 mL each of 10% NaHCO3, H2O, and brine. The organic layer was separated, dried over Na2SO4, filtered, and concentrated in vacuo to yield 1-(2-nitrophenyl)-4-benzylpiperazine (30 g). Calc'd for C17H19N3O2: 297.15.

Workup

  1. customTo a 500 mL round-bottomed flask equipped
  2. stirringThe reaction was stirred for 18 h
  3. washwashed with 300 mL each of 10% NaHCO3, H2O, and brine
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7bc5c90048ff4a84836987590020e6cc
Source dataset
uspto-grants-2006_10
Patent number
US07115607B2

Reaction notes

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