Tetrahydrofuran → [4-(2,4-Dimethylphenyl)piperazin-1-yl](4-iodophenyl)methanone

HRID 1803939Notes

Reaction equation

HRID 1803939 reaction equation
O1CCCC1.[I: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]([I:6])=[CH:8][CH:9]=2)=[O:12])[CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 705441-(2,4-Xylyl)piperazineHCID 743734-Iodobenzoyl chloride

Product 1

HCID 58484733[4-(2,4-Dimethylphenyl)piperazin-1-yl](4-iodophenyl)methanoneYield 101.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To tetrahydrofuran (60 mL) were added 4-iodobenzoyl chloride (5 g), 1-(2,4-dimethylphenyl)piperazine (3.6 g) and 1N aqueous sodium hydroxide solution (20 mL), and the mixture was stirred at room temperature overnight. Ethyl acetate was added for partitioning, the organic layer was washed with saturated brine, and the solvent was evaporated. The title compound (8 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-cc3d32c8e2ab49d7b226489d80053ed9
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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