4-Nitrobenzoic Acid → (4-Methylpiperazin-1-yl)(4-nitrophenyl)methanone

HRID 2092518Notes

Reaction equation

HRID 2092518 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][N:14]([CH:16]=O)[CH3:15].C1C=CC2N(O)N=NC=2C=1.C[CH2:29][N:30]=[C:31]=NCCCN(C)C.Cl>O>[CH3:13][N:14]1[CH2:16][CH2:31][N:30]([C:8]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)=[O:10])[CH2:29][CH2:15]1

Participants

6

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 716396(4-Methylpiperazin-1-yl)(4-nitrophenyl)methanoneYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-nitro-benzoic acid (10 g, 0.0598 mol) in DMF (300 mL) 1-methyl-piperazine (7.19 g, 0.0718 mol), HOBt (10.5 g, 0.0777 mol), EDC.HCl (17.12 g, 0.0897 mol) and TEA (12.1 g, 0.1196 mol) were added. The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate (3×200 mL). The organic layer was washed with water, brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford the title compound [14 g, 95%]; LC-MS (ESI): Calculated mass: 249.1; Observed mass: 250.0 [M+H]+ (RT: 0.10 min).

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-842e2a06d41c4c13b82cdec44425fde0
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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