2-[4-(Trifluoromethyl)phenyl]pyrazine → 2-[4-(Trifluoromethyl)phenyl]piperazine

HRID 1869769Notes

Reaction equation

HRID 1869769 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1>C(O)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH2:11][NH:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 50458142-[4-(Trifluoromethyl)phenyl]pyrazine

Product 1

HCID 36591772-[4-(Trifluoromethyl)phenyl]piperazine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 176Acetic AcidSolvent

Procedure

The pyrazine from Step 1 (13 g, 0.058 mol) was dissolved in acetic acid (100 mL) and palladium acetate added. This mixture was hydrogenated at 45 psi for 4 h., then filtered to remove catalyst and the filtrate concentrated in vacuo to give the product as brown solid. 1H NMR (500 MHz, CD3OD): δ 1.98 (6H, s), 2.93 (1H, t, J 11.9), 3.03-3.15 (2H, m), 3.26-3.32 (3H, m), 4.09 (1H, dd, J 2.7, 11.2), 7.65 (2H, d, J 8.3), 7.72 (2H, d, J 8.2).

Workup

  1. filtrationfiltered
  2. customto remove catalyst
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-53981fa1b1f94907843288875bca9974
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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