1-Isopropyl-4-(6-nitropyridin-3-yl)piperazine → 5-(4-(Propan-2-yl)piperazin-1-yl)pyridin-2-amine

HRID 449609Notes

Reaction equation

HRID 449609 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[N:12][C:13]([N+:16]([O-])=O)=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]>CCO.[Pd]>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[N:12][CH:11]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 575020971-Isopropyl-4-(6-nitropyridin-3-yl)piperazine

Product 1

HCID 434619445-(4-(Propan-2-yl)piperazin-1-yl)pyridin-2-amineYield 61.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 250 mL round-bottomed flask, 1-isopropyl-4-(6-nitropyridin-3-yl)piperazine (788 mg, 3.15 mmol, Eq: 1.00) in EtOH (40 ml) was combined with palladium on carbon (DeGussa)(78.2 mg, 735 μmol, Eq: 0.233). The mixture was evacuated twice with hydrogen and then stirred under a hydrogen atmosphere for 18 h. The solution was filtered through celite, rinsing the celite with fresh ethanol. The solvent was evaporated under reduced pressure to give 5-(4-isopropylpiperazin-1-yl)pyridin-2-amine (425 mg, 61%). LC/MS-ESI observed [M+H]+ 221.

Workup

  1. customThe mixture was evacuated twice with hydrogen
  2. filtrationThe solution was filtered through celite
  3. washrinsing the celite with fresh ethanol
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-141944ccc63f4873b599b9cf47ff11dc
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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