Sodium hydride → HCID 23081564, compound

HRID 856040Notes

Reaction equation

HRID 856040 reaction equation
[H-].[Na+].[O:3]=[C:4]1[NH:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1.[F:17][C:18]([F:28])([F:27])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C=O)C>[O:3]=[C:4]1[N:9]([CH2:23][C:22]2[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:27])[F:28])=[CH:26][CH:25]=2)[CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 123096p-Trifluoromethylbenzyl chlorideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 23081564HCID 23081564, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (840 mg, 24.5 mmol) was gradually added to a solution of tert-butyl 3-oxopiperazine-1-carboxylate (4.1 g, 20.4 mmol) in DMF (30 ml) while cooling in an ice-bath, and the mixture was stirred at room temperature for 30 minutes. A solution of 4-trifluoromethylbenzyl chloride (5 g, 20.9 mmol) in DMF (5 ml) was added dropwise to the mixture while cooling in an ice-bath, which was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate twice. The extract was washed with water twice and brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride) to afford tert-butyl 3-oxo-4-(4-trifluoromethylbenzyl)piperazine-1-carboxylate (6.7 g, yield 91%) as a colorless crystalline powder.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. temperaturewhile cooling in an ice-bath
  3. stirringwhich was stirred at room temperature for 2 hours
  4. extractionextracted with ethyl acetate twice
  5. washThe extract was washed with water twice
  6. dry with materialbrine, and dried over sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-2a15bf37bbc44482ac02d6817e34bde8
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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