1-(4-Nitrophenyl)piperazine → HCID 86646745, compound

HRID 527319Notes

Reaction equation

HRID 527319 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:18]>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]3[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=3)=[O:18])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 804471-(4-Nitrophenyl)piperazineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 86646745HCID 86646745, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-nitrophenyl)piperazine (0.5 g) and TEA (0.7 mL) in DCM (15 mL) at rt was added 4-nitrophenyl chloroformate (0.7 g). The reaction mixture was stirred at rt for 18 h and then partitioned between DCM and ice-water. The separated aqueous layer was extracted with DCM thrice and the pooled organic extracts was washed with water and sat'd NaCl, dried over anhyd. Na2SO4, filtered, and conc. in vacuo to give the crude product as a yellow solid which was recrystallized from DCM and diisopropylether to give 4-nitrophenyl 4-(4-nitrophenyl)piperazine-1-carboxylate as a bright yellow powder (Y=0.8 g, 89%).

Workup

  1. custompartitioned between DCM and ice-water
  2. extractionThe separated aqueous layer was extracted with DCM thrice
  3. washthe pooled organic extracts was washed with water
  4. customdried over anhyd
  5. filtrationNa2SO4, filtered
  6. customconc. in vacuo to give the crude product as a yellow solid which
  7. customwas recrystallized from DCM and diisopropylether

Sources & evidence

ORD record
ord-d2954cd3dbed4337bf78c6e5b75b5789
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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