Water → 1-(2-Methyl-2-oxiranylmethyl)-4-(4-trifluoromethylphenyl)piperazine

HRID 856119Notes

Reaction equation

HRID 856119 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[F:9][C:10]([F:28])([F:27])[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24](=[O:26])[CH3:25])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.O>CS(C)=O>[CH3:25][C:24]1([CH2:23][N:20]2[CH2:19][CH2:18][N:17]([C:14]3[CH:13]=[CH:12][C:11]([C:10]([F:9])([F:27])[F:28])=[CH:16][CH:15]=3)[CH2:22][CH2:21]2)[CH2:2][O:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 230812711-{4-(4-Trifluoromethylphenyl)piperazin-1-yl}propan-2-one

Product 1

HCID 230815381-(2-Methyl-2-oxiranylmethyl)-4-(4-trifluoromethylphenyl)piperazineYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Trimethylsulfoxonium iodide (2.5 g, 11.6 mmol) was gradually added to a suspension of sodium hydride (484 mg, 12.1 mmol) in dimethylsulfoxide (30 ml), and the mixture was stirred at room temperature for 1 hour. To which a solution of 1-{4-(4-trifluoromethylphenyl)piperazin-1-yl}propan-2-one (3.4 g, 11.9 mmol) in dimethylsulfoxide (20 ml) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into iced water, and extracted with diethyl ether. The organic phase was washed with a saturated saline solution, dried over magnesium sulfate, and then filtered. The resultant filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) to afford 1-(2-methyl-2-oxiranylmethyl)-4-(4-trifluoromethylphenyl)piperazine (3.2 g, yield 98%)as a light yellow powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionextracted with diethyl ether
  3. washThe organic phase was washed with a saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe resultant filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)

Sources & evidence

ORD record
ord-3e1b66dc2fec4b7e8e581386edfb98e7
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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