Water → HCID 69480980, compound

HRID 856079Notes

Reaction equation

HRID 856079 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Br[CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([CH2:18][CH2:19][N:20]3[C:24](=[O:25])[C:23]4=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]4[C:21]3=[O:30])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 1217181-(4-(Trifluoromethyl)phenyl)piperazine

Product 1

HCID 69480980HCID 69480980, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(4-trifluoromethylphenyl)piperazine (5.2 g, 22.59 mmol), N-(2-bromoethyl)phthalimide (5.22 g, 20.53 mmol) and potassium carbonate (3.36 g, 24.28 mmol) in DMF (30 ml) was stirred at 100° C. for 2 hours. The reaction mixture was allowed to return to room temperature, to which water was added, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=50/1), and the resulting solid was washed with methanol, and then dried in vacuo to afford N-{2-[4-(4-trifluoromethylphenyl)piperazin-1-yl]ethyl}phthalimide (4.85 g, yield 53%) as a white powder.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=50/1)
  8. washthe resulting solid was washed with methanol
  9. customdried in vacuo

Sources & evidence

ORD record
ord-db2dfeada5644fcba67a497a7cbdb621
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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