1-Ethyl-4-(6-nitropyridin-3-yl)piperazine → 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine

HRID 1918872Notes

Reaction equation

HRID 1918872 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)[CH2:5][CH2:4]1)[CH3:2]>[Pd].CCO>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[N:11][CH:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

4

Reactant 1

HCID 575020861-Ethyl-4-(6-nitropyridin-3-yl)piperazine

Product 1

HCID 284115995-(4-Ethylpiperazin-1-yl)pyridin-2-amineYield 111%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a hydrogenation bottle, 138a (2.59 g, 10.96 mmol), EtOH (100 mL), 10% Pd/C (580 mg, 0.55 mmol) were added. The mixture was hydrogenated at 55 psi for 2 hrs, and then filtered through celite and washed with MeOH (20 mL). The solvent was removed in vacuo and pink solids were obtained as 138b (2.51 g, 82%).

Workup

  1. filtrationfiltered through celite
  2. washwashed with MeOH (20 mL)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d47019a9a642470188d9ff8a4908feb5
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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