tert-Butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate → 1,1-Dimethylethyl 4-(4-amino-2-fluorophenyl)-1-piperazinecarboxylate

HRID 57557Notes

Reaction equation

HRID 57557 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1>CO.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:13][CH2:12]2)=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 1

HCID 16203508tert-Butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 162036301,1-Dimethylethyl 4-(4-amino-2-fluorophenyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of tert-butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate (5 mmol) in MeOH (30 mL) was added Pd/C (1 g), then the mixture was stirred for 18 hours at 20° C. under 1 atm. H2. The reaction was filtered and concentrated to give gray yellow oil. MS (m/z): 296 (M+H)+

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customto give gray yellow oil

Sources & evidence

ORD record
ord-87e51de047cb434cb15f48580213071b
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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