Ethyl Acetate → (2R)-4-benzyl-1-(3,5-dichlorobenzoyl)-2-(1H-indol-3-yl-methyl)piperazine

HRID 1379188Notes

Reaction equation

HRID 1379188 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@H:10]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:30][C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([Cl:40])[CH:39]=1)[C:34](Cl)=[O:35].C(OCC)(=O)C>CN(C)C=O.O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:34](=[O:35])[C:33]2[CH:32]=[C:31]([Cl:30])[CH:39]=[C:38]([Cl:40])[CH:37]=2)[C@H:10]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 761913,5-Dichlorobenzoyl chlorideHCID 53910379(3R)-1-benzyl-3-(1H-indol-3-yl-methyl)piperazine

Product 1

HCID 54039029(2R)-4-benzyl-1-(3,5-dichlorobenzoyl)-2-(1H-indol-3-yl-methyl)piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled mixture of (3R)-1-benzyl-3-(1H-indol-3-yl-methyl)piperazine (305 mg) and potassium carbonate (207 mg) in dimethylformamide (1 ml) was added 3,5-dichlorobenzoyl chloride (210 mg). The mixture was stirred at room temperature for 1 hour. Ethyl acetate and water were added. The organic layer was washed successively with aqueous sodium bicarbonate solution and brine and dried over magnesium sulfate. After evaporation of the solvent, the residue was dissolved in ethyl ether. After insoluble material was removed by filtration, the filtrate was concentrated under reduced pressure and the residue was triturated with diisopropyl ether, collected by filtration and dried to give (2R)-4-benzyl-1-(3,5-dichlorobenzoyl)-2-(1H-indol-3-yl-methyl)piperazine.

Workup

  1. washThe organic layer was washed successively with aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over magnesium sulfate
  3. customAfter evaporation of the solvent
  4. dissolutionthe residue was dissolved in ethyl ether
  5. customAfter insoluble material was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was triturated with diisopropyl ether
  8. filtrationcollected by filtration
  9. customdried

Sources & evidence

ORD record
ord-fe275ec4e18b4f1291b13ac100ee79a1
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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