1-Methyl-4-{[4-nitro-2-(trifluoromethyl)phenyl]methyl}piperazine → AP-24592

HRID 535835Notes

Reaction equation

HRID 535835 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)phenyl]methyl}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 (1H, d, J=9.0 Hz), 6.91 (1H, s), 6.77-6.80 (1H, d J=9.0 Hz), 3.77 (2H, s), 3.54 (2H, s), 2.53 (8H, brs), 2.34 (3H, s).

Workup

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

Sources & evidence

ORD record
ord-e1fefc6736ea4d7982d4fc2603595322
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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