Sodium Iodide → HCID 71295490, compound

HRID 1774683Notes

Reaction equation

HRID 1774683 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13](=[O:22])[N:14]2[CH2:17][O:18][C:19](=[O:21])[CH3:20])=[CH:9][CH:8]=1.Cl.[S:24]1[CH:28]=[CH:27][C:26]2[C:29]([N:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[CH:30][CH:31]=[CH:32][C:25]1=2.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[S:24]1[CH:28]=[CH:27][C:26]2[C:29]([N:33]3[CH2:38][CH2:37][N:36]([CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]4[CH:16]=[C:15]5[C:10]([CH:11]=[CH:12][C:13](=[O:22])[N:14]5[CH2:17][O:18][C:19](=[O:21])[CH3:20])=[CH:9][CH:8]=4)[CH2:35][CH2:34]3)=[CH:30][CH:31]=[CH:32][C:25]1=2

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 574825411-(1-Benzothiophen-4-yl)piperazine hydrochlorideHCID 89428632HCID 89428632, compound

Product 1

HCID 71295490HCID 71295490, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Acetic acid 7-(4-chlorobutoxy)-2-oxo-2H-quinolin-1-ylmethyl ester (299 mg), 1-benzo[b]thiophen-4-ylpiperazine hydrochloride (235 mg), potassium carbonate (319 mg) and sodium iodide (152 mg) were suspended in DMF (5 ml), and this was stirred at 70° C. for 3 hr and further at 80° C. for 4 hr. After cooling to room temperature, to the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by moderate-pressure silica gel column chromatography (hexane:ethyl acetate=1:0 to 1:9) and further by basic silica gel column chromatography, and concentrated under reduced pressure to give the title compound (132 mg) as a colorless amorphous solid.

Workup

  1. temperatureAfter cooling to room temperature, to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by moderate-pressure silica gel column chromatography (hexane:ethyl acetate=1:0 to 1:9) and further by basic silica gel column chromatography
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-983518035d5e43d082342669df25b104
Source dataset
uspto-grants-2016_02
Patent number
US09260420B2

Reaction notes

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