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

HRID 1622511Notes

Reaction equation

HRID 1622511 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.C([O-])(O)=O.[Na+]>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 8471TriethylamineHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 468387611-(Bromomethyl)-4-nitro-2-(trifluoromethyl)benzene

Product 1

HCID 468389061-Methyl-4-{[4-nitro-2-(trifluoromethyl)phenyl]methyl}piperazineYield 72.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 1-(bromomethyl)-4-nitro-2-(trifluoromethyl)benzene (13.33 mmol, 75% pure) in DCM (10 mL) was added Et3N (1.4 mL, 10 mmol) and 1-methylpiperazine (1.1 mL, 10 mmol). After stirring for 3 h at rt, aq. NaHCO3 was added, and the mixture was extracted with DCM. The combined organic layer was dried over Na2SO4, filtered, concentrated, and the resulting residue was purified by silica gel chromatography (eluted with 10% MeOH/DCM) to provide 2.21 g of product as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with DCM
  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 (eluted with 10% MeOH/DCM)

Sources & evidence

ORD record
ord-8e78af40d483401ab0d77b3dc6f16b59
Source dataset
uspto-grants-2014_07
Patent number
US08778942B2

Reaction notes

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