1-Methyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine → AP-24592
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]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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).