Benzyl Bromide → HCID 66792821, compound

HRID 534924Notes

Reaction equation

HRID 534924 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([CH:19]2[NH:23][C:22](=[O:24])[CH2:21][CH2:20]2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[CH2:27]([N:23]1[CH:19]([C:17]([N:14]2[CH2:13][CH2:12][N:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:16][CH2:15]2)=[O:18])[CH2:20][CH2:21][C:22]1=[O:24])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 66750924HCID 66750924, compound

Product 1

HCID 66792821HCID 66792821, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 5-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}pyrrolidin-2-one obtained in Example 62 (0.30 g, 0.91 mmol) in DMF (5 mL) was added sodium hydride (40 mg, 60% in mineral oil, 1.00 mmol) and the mixture was stirred at room temperature for 30 min. After this time, to the mixture was added benzyl bromide (0.17 g, 1.00 mmol) and the mixture was stirred at room temperature for 2 h. The reaction was quenched with saturated ammonium chloride solution, and the mixture was partitioned between ethyl acetate and water, and the organic layer was washed with water, saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting solid was triturated with hexane-diisopropyl ether solution to give the title compound (0.30 g, 79%) as a white solid, mp 164° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. customthe mixture was partitioned between ethyl acetate and water
  4. washthe organic layer was washed with water, saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting solid was triturated with hexane-diisopropyl ether solution

Sources & evidence

ORD record
ord-a4a46f1255ab40ab8252540feaa49f06
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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