Potassium Iodide → HCID 23291085, compound

HRID 365309Notes

Reaction equation

HRID 365309 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:17]=[CH:16][C:9]2[NH:10][C:11](=[O:15])[CH2:12][S:13](=[O:14])[C:8]=2[CH:7]=1.[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[CH2:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[CH2:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:17]=[CH:16][C:9]3[NH:10][C:11](=[O:15])[CH2:12][S:13](=[O:14])[C:8]=3[CH:7]=2)[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 43753132-(1-Piperazinylmethyl)quinolineHCID 23291097HCID 23291097, compound

Product 1

HCID 23291085HCID 23291085, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture consisting of 7-(3-chloropropoxy)-3,4-dihydro-2H-1,4-benzothiazin-3-one-1-oxide (2.02 g, 7.38 mmol), N-(2-quinolylmethyl)piperazine (2.52 g, 11.07 mmol), potassium carbonate (2.04 g, 14.76 mmol), potassium iodide (2.45 g, 14.76 mmol) and DMF (50 ml) was stirred at 80° C. for 4 hours. The solvent was distilled off from the reaction mixture under reduced pressure, followed by the addition of water. The resulting mixture was extracted with chloroform-methanol (10:1). The extract was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column while using chloroform-ammonia-saturated methanol (10:1) as an eluent. Fractions containing the target compound were collected and then concentrated under reduced pressure, whereby 1.23 g of the title compound was obtained as a yellow oil (4.49 mmol, 60.9%).

Workup

  1. distillationThe solvent was distilled off from the reaction mixture under reduced pressure
  2. additionfollowed by the addition of water
  3. extractionThe resulting mixture was extracted with chloroform-methanol (10:1)
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column
  7. additionFractions containing the target compound
  8. customwere collected
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3376ad834f6d4f3eb24a02d96a54ef7e
Source dataset
uspto-grants-2000_10
Patent number
US06127360

Reaction notes

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