Tetrahydrofuran → (4-Bromophenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanone

HRID 1803944Notes

Reaction equation

HRID 1803944 reaction equation
O1CCCC1.[Br:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.[OH-].[Na+]>C(OCC)(=O)C>[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[N:24]1[CH2:25][CH2:26][N:27]([C:11]([C:10]2[CH:14]=[CH:15][C:7]([Br:6])=[CH:8][CH:9]=2)=[O:12])[CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 685154-Bromobenzoyl chlorideHCID 705441-(2,4-Xylyl)piperazine

Product 1

HCID 58484623(4-Bromophenyl)[4-(2,4-dimethylphenyl)piperazin-1-yl]methanoneYield 72.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To tetrahydrofuran (120 mL) were added 4-bromobenzoyl chloride (25 g), 1-(2,4-dimethylphenyl)piperazine (22 g) and 1N aqueous sodium hydroxide solution (120 mL), and the mixture was stirred at room temperature for 6 hr. Ethyl acetate was added for partitioning, the organic layer was washed with saturated brine, and the solvent was evaporated. The title compound (31 g) was obtained.

Workup

  1. customfor partitioning
  2. washthe organic layer was washed with saturated brine
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5b3fdafddb364730ad69bcab19936c72
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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