1-Methyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine → AP-24592

HRID 706821Notes

Reaction equation

HRID 706821 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[C:18]([F:21])([F:20])[F:19])[CH2:4][CH2:3]1>CO.[Ni]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=2[C:18]([F:21])([F:19])[F:20])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 468389061-Methyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine

Product 1

HCID 46838908AP-24592Yield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Into a solution 4-methyl-1-(4-nitro-2-(trifluoromethyl)benzyl)piperazine (1.5 g, 5 mmol) in MeOH (250 mL) was added Raney Nickel (0.15 g, 10 wt %). The suspension was stirred under hydrogen atmosphere (50 psi) for 24 hrs and monitored by TLC. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to yield the desired product (1.36 g, 100%).1H NMR (300 MHz, CDCl3) δ: 7.43-7.46 (1 H, d, J=9.0 Hz), 6.91 (1 H, s), 6.77-6.80 (1 H, d J=9.0 Hz), 3.77 (2 H, s), 3.54 (2 H, s), 2.53 (8H, brs), 2.34 (3 H, s).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0ad2cae6829b49dbb5c7358b35de5631
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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