Water → (4-Bromo-2-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 2411245Notes

Reaction equation

HRID 2411245 reaction equation
[CH3:1][C:2]1[C:3]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[C:18]([F:25])[CH:17]=1.[OH-].[Na+].O>O1CCCC1>[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:12]2[CH2:11][CH2:10][N:9]([C:3]3[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]=3)[CH2:14][CH2:13]2)=[O:21])=[C:18]([F:25])[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 27340264-Bromo-2-fluorobenzoyl chlorideHCID 584844961-(3,5-Dimethylpyridin-2-yl)piperazine

Product 1

HCID 58484626(4-Bromo-2-fluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanoneYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3,5-Dimethylpyridin-2-yl)piperazine (2.42 g) described in Preparation Example 79 was dissolved in tetrahydrofuran (32 mL), 4-bromo-2-fluorobenzoyl chloride (3.0 g) and 1N aqueous sodium hydroxide solution (15 mL) were added, and the mixture was stirred at room temperature. The reaction mixture was poured into water under cooling, 4N aqueous sodium hydroxide solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine added 4N aqueous sodium hydroxide solution and saturated brine, dried over sodium sulfate, and the solvent was evaporated. The obtained residue was purified by column chromatography (ethyl acetate:hexane) to give the title compound (4.39 g).

Workup

  1. temperatureunder cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. additionadded 4N aqueous sodium hydroxide solution and saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-f75c167971a24a8c8f9873ee6337da49
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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