Piperazine → 1-((2-(Trifluoromethyl)phenyl)methyl)piperazine

HRID 1917090Notes

Reaction equation

HRID 1917090 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([F:18])([F:17])[F:16].C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:16][C:15]([F:17])([F:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzene

Product 1

HCID 30233221-((2-(Trifluoromethyl)phenyl)methyl)piperazineYield 68.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.08 g (12.5 mmol) of piperazine are placed in the presence of 1 g (4.2 mmol) of 1-bromomethyl-2-trifluoromethyl-benzene and 0.64 mL (4.6 mmol) of triethylamine in 10 mL of toluene. The reaction medium is stirred for 30 min at room temperature and then heated to 110° C. for 6 h. After dry concentration, the obtained residue is taken up with AcOEt and washed with water. After drying on MgSO4, the organic phases are dry concentrated, the obtained residue is purified by flash chromatography on silica (CH2Cl2-MeOH—NH4OH: 90-9-1). 0.7 g of intermediate 7a are thereby isolated as a clear oil (yield 68%).

Workup

  1. temperatureheated to 110° C. for 6 h
  2. customAfter dry
  3. concentrationconcentration
  4. washwashed with water
  5. customAfter drying on MgSO4
  6. customthe organic phases are dry
  7. concentrationconcentrated
  8. customthe obtained residue is purified by flash chromatography on silica (CH2Cl2-MeOH—NH4OH: 90-9-1)

Sources & evidence

ORD record
ord-4836326672db4340a251e84a74df417a
Source dataset
uspto-grants-2013_12
Patent number
US08618287B2

Reaction notes

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