4-Methyl-3-nitrobenzoic acid → (4-Ethylpiperazin-1-yl)-(4-methyl-3-nitrophenyl)methanone

HRID 912153

Reaction equation

HRID 912153 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C1C=CC2N(O)N=NC=2C=1.[CH2:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[CH3:25]>ClCCl>[CH2:24]([N:26]1[CH2:31][CH2:30][N:29]([C:6]([C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)=[O:8])[CH2:28][CH2:27]1)[CH3:25]

Participants

5

Reactant 3

HCID 73194-Methyl-3-nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 791961-Ethylpiperazine

Product 1

HCID 808340(4-Ethylpiperazin-1-yl)-(4-methyl-3-nitrophenyl)methanoneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-methyl-3-nitro-benzoic acid (730 mg, 4.03 mmol), WSCI (930 mg, 4.85 mmol), HOBt (110 mg, 0.674 mmol) and N-ethylpiperazine (608 μl, 4.79 mmol), dichloromethane (8 ml) was added, followed by stirring for 13 hours. The reaction mixture was washed with aqueous ammonium chloride solution, and subsequently dried over sodium sulfate. After filtering sodium sulfate, the filtrate was concentrated under reduced pressure, to obtain (4-ethyl-piperazin-1-yl)-(4-methyl-3-nitro-phenyl)-methanone (1.06 g, 95%).

Workup

  1. washThe reaction mixture was washed with aqueous ammonium chloride solution
  2. dry with materialsubsequently dried over sodium sulfate
  3. filtrationAfter filtering sodium sulfate
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8036c311c9f7474e8a9ec5c3ab79236f
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Linked notes

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