1-(4-(6-Nitropyridin-3-YL)piperazin-1-YL)ethan-1-one → 1-(4-(6-Aminopyridin-3-YL)piperazin-1-YL)ethan-1-one

HRID 592154Notes

Reaction equation

HRID 592154 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:18])[CH3:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:18])[CH3:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 47806861-(4-(6-Nitropyridin-3-YL)piperazin-1-YL)ethan-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 284116891-(4-(6-Aminopyridin-3-YL)piperazin-1-YL)ethan-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a round-bottom flask was added 1-(4-(6-nitropyridin-3-yl)piperazin-1-yl)ethanone 111-3 (2.6 g, 10.4 mmol), Pd/C (0.5 g) and methanol (50 mL). The reaction was stirred for 4 hours under hydrogen atmosphere by attaching a hydrogen balloon. The reaction was flashed with nitrogen and the solid was removed by filtration. The solvent was removed by rotary evaporation. The crude product was purified by silica-gel flash chromatography to give 1-(4-(6-aminopyridin-3-yl)piperazin-1-yl)ethanone 111-4 as an off-white solid. MS m/z 221.1 (M+1). 1H NMR 400 MHz (DMSO-d6) δ7.62 (d, 1H, J=2.8 Hz), 7.20 (dd, 1H, J1=8.8 Hz, J2=2.8 Hz), 6.41 (d, 1H, J=8.8 Hz), 5.47 (s, 2H), 3.55 (m, 4H), 2.93 (t, 2H, J=5.2 Hz), 2.86 (t, 2H, J=5.2 Hz), 2.03 (s, 3H).

Workup

  1. customthe solid was removed by filtration
  2. customThe solvent was removed by rotary evaporation
  3. customThe crude product was purified by silica-gel flash chromatography

Sources & evidence

ORD record
ord-3e5b9b13d8824875b2fc88beb4e69e18
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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