Tert-butyl 4-(3-methoxy-4-nitrophenyl)piperazine-1-carboxylate → Tert-butyl 4-(4-amino-3-methoxyphenyl)piperazine-1-carboxylate

HRID 1503813Notes

Reaction equation

HRID 1503813 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>[Ni].CO>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:14][CH2:13]2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 25918710Tert-butyl 4-(3-methoxy-4-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 67128946Tert-butyl 4-(4-amino-3-methoxyphenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of the product of Example 13A (6.3 g, 18.7 mmol) and Raney nickel (2.0 g) in 300 mL methanol was stirred under hydrogen at ambient temperature for 5 hours. The mixture was filtered through diatomaceous earth and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with a gradient of 2/1 to 1/1 petroleum/ethyl acetate to give the title compound.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  4. washeluting with a gradient of 2/1 to 1/1 petroleum/ethyl acetate

Sources & evidence

ORD record
ord-c1c8820c536b408fac6aebf9a2452163
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

Loading…