1-Boc-4-(4-Nitrophenyl)piperazine → tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylate

HRID 1778947Notes

Reaction equation

HRID 1778947 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>CCOC(C)=O.[Pd]>[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

4

Reactant 1

HCID 33806961-Boc-4-(4-Nitrophenyl)piperazine

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A slurry of 10% Pd/C (0.500 g) in EtOAc (10 mL) was added to a solution of tert-butyl 4-(4-nitrophenyl)piperazine-1-carboxylate (I4) (3.24 g, 10.5 mmol) in EtOAc (90 mL) and the resulting suspension was stirred under a hydrogen atmosphere for 42 hours at room temperature. The catalyst was removed by filtration through Celite, washing with EtOAc (7×10 mL), then the filtrate was evaporated to dryness to give the title compound K3 as a pale pink solid (2.92 g, 99%); 1H NMR (400 MHz, d6-DMSO) δ 6.72-6.66 (m, 2H), 6.52-6.45 (m, 2H), 4.60 (s, 2H), 3.44-3.39 (m, 4H), 2.87-2.79 (m, 4H), 1.41 (s, 9H). LCMS-A: rt 4.40 min; m/z 278.2 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. washwashing with EtOAc (7×10 mL)
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-149bb57c41df4a47b6d04ec5af3fcbe7
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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