Potassium Iodide → HCID 68855468, compound

HRID 1984008Notes

Reaction equation

HRID 1984008 reaction equation
[Cl:1][CH2:2][C:3]([NH2:5])=[O:4].[NH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[NH:28][CH:27]=[CH:26]4)[CH2:19][CH2:18]2)[CH2:7]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.CC(=O)CC>[ClH:1].[ClH:1].[NH:28]1[C:29]2[C:25](=[CH:24][C:23]([N:20]3[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][C@H:8]4[C:9]5[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=5)[N:6]([CH2:2][C:3]([NH2:5])=[O:4])[CH2:7]4)[CH2:18][CH2:19]3)=[CH:31][CH:30]=2)[CH:26]=[CH:27]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 68854443HCID 68854443, compound

Product 1

HCID 68855468HCID 68855468, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a clear solution of 2-chloroacetamide (17.7 g, 0.19 mol) in N-methylpyrrolidin-2-one (500 mL) was slowly added a solution of 5-{4-[(S)-2-(2,3-dihydro-1H-indol-3-yl)-ethyl]-piperazin-1-yl}-1H-indole (52.6 g, 0.15 mol) in butanone (600 mL). Potassium iodide (29.0 g, 0.17 mol) and potassium carbonate (31.4 g, 0.15 mol) was added and the resulting mixture was boiled under reflux for 1 h, filtered and poured onto a mixture of ice and brine. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate/ethanol/triethylamine 70:5:5) to give crude title compound (30.6 g). This was precipitated from methanol by addition of hydrochloric acid in diethyl ether until pH was approximately 3. The compound was collected by filtration as a powder (7.7 g). Assignment of the optical rotation was done in dimethyl sulfoxide.

Workup

  1. temperatureunder reflux for 1 h
  2. filtrationfiltered
  3. additionpoured onto a mixture of ice and brine
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washthe combined organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (ethyl acetate/ethanol/triethylamine 70:5:5)

Sources & evidence

ORD record
ord-5d6d2ec7877a4fd7b10dec5246c473db
Source dataset
uspto-grants-2009_06
Patent number
US07544685B2

Reaction notes

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