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

HRID 535834Notes

Reaction equation

HRID 535834 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].CCN(CC)CC.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.O>C(Cl)Cl>[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[C:12]([F:15])([F:14])[F:13])[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 468387611-(Bromomethyl)-4-nitro-2-(trifluoromethyl)benzene

Product 1

HCID 468389061-Methyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazineYield 67.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 1-(bromomethyl)-2-(trifluoromethyl)-4-nitrobenzene (13.7 mmol, 60% pure) in CH2Cl2 (20 mL) was added Et3N (1.5 g, 15 mmol) and 4-methylpiperazine (1.5 g, 15 mmol). After stirring for 5 hrs at rt, 50 mL H2O was added, and the mixture was extracted with 50 mL CH2Cl2. The combined organic layer was dried over Na2SO4, filtered, concentrated, and the resulting residue was purified by silica gel chromatography (eluent: 10% MeOH in CH2Cl2) to give the product (67.4%, 2.8 g). 1H NMR (300 MHz, CDCl3) δ: 8.52 (1H, s), 8.37-8.40 (1H, d, J=9.0 Hz), 8.00-8.03 (1H, d, J=9.0 Hz), 3.85 (2H, s), 3.09-3.15 (2H, m), 2.90-2.93 (2H, m), 2.80-2.83 (2H, m), 2.67 (3H, s), 2.53-2.59 (2H, m).

Workup

  1. extractionthe mixture was extracted with 50 mL CH2Cl2
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe resulting residue was purified by silica gel chromatography (eluent: 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-95b7bb4d13894ba886b37747d33ac322
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

Loading…