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

HRID 2411239Notes

Reaction equation

HRID 2411239 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 and the mixture was partitioned. The organic layer was washed with saturated brine, and the solvent was evaporated to give the title compound (8 g).

Workup

  1. customthe mixture was partitioned
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2be8a1c8e3824d3ea1c5bbcc67bb13e8
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

Loading…