HCID 21114528, compound → HCID 21114527, compound

HRID 1767753Notes

Reaction equation

HRID 1767753 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][N:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2]>[Pd].C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][N:16]=3)[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 1

HCID 21114528HCID 21114528, compound

Product 1

HCID 21114527HCID 21114527, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (25 mg, 0.024 mmol) was added to a stirred suspension of 1-(4-cyanophenyl)-4-(5-nitropyridin-2-yl)-piperazine (150 mg, 0.48 mmol) in ethanol (50 ml) at ambient temperature and the reaction stirred for 6 hours under an atmosphere of hydrogen. The reaction was filtered through a pad of celite and the solvent evaporated in vacuo. Purification by flash chromatography on alumina, eluting with 0.5% methanol in dichloromethane yielded 1-(4-cyanophenyl)-4-(5-aminopyridin-2-yl)piperazine (100 mg, 74% yield):

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. customthe solvent evaporated in vacuo
  3. customPurification by flash chromatography on alumina
  4. washeluting with 0.5% methanol in dichloromethane

Sources & evidence

ORD record
ord-9b005675e71c476f8db285db7a1ef8e7
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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