Sodium Carbonate → Ethyl 4-(4-(2-nitrobenzyl)piperazin-1-yl)benzoate

HRID 1798430Notes

Reaction equation

HRID 1798430 reaction equation
[N:1]1([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N+:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][CH:17]=2)[CH2:6][CH2:5]1)([O-:28])=[O:27]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 77569alpha-Bromo-2-nitrotolueneHCID 2761178Ethyl 4-(piperazin-1-yl)benzoate

Product 1

HCID 57474940Ethyl 4-(4-(2-nitrobenzyl)piperazin-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 4-(piperazin-1-yl)benzoate (1.5 g), 1-(bromomethyl)-2-nitrobenzene (1.383 g) and sodium carbonate (2.036 g) were suspended in anhydrous N,N-dimethylformamide (20 mL) at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate, washed with water and brine, and concentrated. The residue was purified by flash column purification with 10-40% ethyl acetate/hexane to afford the title compound.

Workup

  1. washwashed with water and brine
  2. concentrationconcentrated
  3. customThe residue was purified by flash column purification with 10-40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f53c2071b66a47df9773b380a001f4b0
Source dataset
uspto-grants-2013_01
Patent number
US08343967B2

Reaction notes

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