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

HRID 1473112Notes

Reaction equation

HRID 1473112 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 235069461-Boc-4-(4-Nitrobenzyl)piperazine

Product 1

HCID 12045001tert-Butyl 4-((4-aminophenyl)methyl)piperazine-1-carboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(4-nitrobenzyl)piperazine-1-carboxylate (I92) (0.500 g, 1.56 mmol), ethyl acetate (100 mL) and 10% Pd/C (150 mg) were agitated under a hydrogen atmosphere at 50 psi. After two hours the mixture was filtered through celite and concentrated. The residue was chromatographed (12 g silica cartridge, 0-60% ethyl acetate/petroleum benzine 40-60° C.) to give the title compound (I93) (327 mg, 72% yield) as a white solid; 1H NMR (400 MHz, CDCl3) δ 7.11-7.05 (m, 2H), 6.67-6.61 (m, 2H), 3.62 (s, 2H), 3.43-3.37 (m, 6H), 2.40-2.30 (m, 4H), 1.45 (s, 9H). LCMS Method C: rt 1.80 min; m/z 292.1 [M+H]+.

Workup

  1. filtrationAfter two hours the mixture was filtered through celite
  2. concentrationconcentrated
  3. customThe residue was chromatographed (12 g silica cartridge, 0-60% ethyl acetate/petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-36def81fed594b27b6dbbaefd3d6f16f
Source dataset
uspto-grants-2015_04
Patent number
US09012461B2

Reaction notes

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