Acetic Acid → tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

HRID 2236411Notes

Reaction equation

HRID 2236411 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.C(O)(=O)C>[Fe].CO>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 33806961-Boc-4-(4-Nitrophenyl)piperazine

Product 1

HCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 4-(4-nitrophenyl)piperazine-1-carboxylate (307 mg, 1 mmol), iron powder (196 mg, 3.5 mmol), acetic acid (0.4 mL, 7 mmol) and methanol (5 mL) is heated at 66 C until no nitro compound left. After it is dried it is treated with ethyl acetate and water, and filtered through a pad of celite. The ethyl acetate layer is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, and then dried to yield the title compound.

Workup

  1. waitleft
  2. customAfter it is dried it
  3. additionis treated with ethyl acetate and water
  4. filtrationfiltered through a pad of celite
  5. washThe ethyl acetate layer is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  6. customdried

Sources & evidence

ORD record
ord-9be49a8221a44f61a126fe3023510246
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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