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

HRID 43055Notes

Reaction equation

HRID 43055 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]>[Pd].CO>[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

4

Reactant 1

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

Product 1

HCID 11011301tert-Butyl 4-(4-aminophenyl)piperazine-1-carboxylateYield 96.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4-(4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (Step 8.3) (1.26 g, 4.1 mmol) and palladium on carbon (200 mg) in MeOH (30 mL) was stirred for 30 min at rt, under a hydrogen atmosphere. The reaction mixture was filtered through a pad of celite and concentrated to afford 1.1 g of the title compound as a pink solid: ESI-MS: 278.2 [M+H]+; tR=2.85 min (System 1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0245bdaea34f4fb5bc1386ff3485f8e2
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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