Trifluoroacetic acid → 1-[2-Methyl-5-(methyloxy)-4-nitrophenyl]piperazine

HRID 1014255Notes

Reaction equation

HRID 1014255 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1.FC(F)(F)C(O)=O.C[O-].[Na+]>ClCCl.CO>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10942334Sodium MethoxideHCID 59441856HCID 59441856, compound

Product 1

HCID 594418321-[2-Methyl-5-(methyloxy)-4-nitrophenyl]piperazineYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1,1-dimethylethyl 4-[2-methyl-5-(methyloxy)-4-nitrophenyl]-1-piperazinecarboxylate (4.8 g, 13.67 mmol) in 80 mL of dichloromethane was added trifluoroacetic acid (˜5.5 mL). The mixture stirred at room temperature for 24 hours. The solvent was rotovaped down. The crude product was taken up in 50 mL of methanol and neutralized with 0.5 N sodium methoxide. 12 g of Silica gel was added and the solvent was rotovaped down. The crude product was purified by flash chromatography to give 1-[2-methyl-5-(methyloxy)-4-nitrophenyl]piperazine (3.43 g, 13.53 mmol, 98%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.75 (s, 1 H), 6.69 (s, 1 H), 3.88 (s, 3 H), 3.08-3.18 (m, 8 H), 2.15-2.21 (m, 3 H).

Workup

  1. addition12 g of Silica gel was added
  2. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-49aa7ccc24a84861a3ca058ab126c3b9
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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