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

HRID 1826583Notes

Reaction equation

HRID 1826583 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Ni].O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 33806961-Boc-4-(4-Nitrophenyl)piperazineHCID 178418361HCID 178418361, compound

Product 1

HCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1.46 g (4.8 mmol) of 4-(4-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester (Example 11) and 1 g of Raney Nickel in 50 mL of tetrahydrofuran is added hydrogen to an initial pressure of 54.5 psi. The reaction is shaken for 14 hours and then filtered. The filtrate is concentrated to give 1.29 g (97%) of the product as a solid.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-03cb6d1798b04518a5fba4a8b19b7f82
Source dataset
uspto-grants-2006_05
Patent number
US07053070B2

Reaction notes

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