Potassium Iodide → HCID 13536203, compound

HRID 1735728Notes

Reaction equation

HRID 1735728 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][C:10](=[O:13])[CH:9]([C:14]([O:16][CH3:17])=[O:15])[S:8][C:7]=2[CH:18]=1.[C:19]1([N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33]Cl)[CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][C:10](=[O:13])[C:9]([CH2:33][CH2:32][CH2:31][N:28]3[CH2:29][CH2:30][N:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:26][CH2:27]3)([C:14]([O:16][CH3:17])=[O:15])[S:8][C:7]=2[CH:18]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 139197Piperazine, 1-(3-chloropropyl)-4-phenyl-HCID 13536177HCID 13536177, compound

Product 1

HCID 13536203HCID 13536203, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of methyl 7-methoxy-3-oxo-3,4-dihydro-2H-1,5-benzoxathiepine-4-carboxylate (10 g), 3-(4-phenylpiperazin-1yl)propyl chloride (9.8 g), anhydrous potassium carbonate (6.2 g), potassium iodide (3.0 g) and methyl ethyl ketone (150 ml) was refluxed under heating for 25 hours. After cooling, inorganic matter was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and dried. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=3:1) to give methyl 7-methoxy-3-oxo-4-[3-(4-phenylpiperazine-1-yl)propyl]-3,4-dihydro-2H-1,5-benzoxathiepine-4-carboxylate. Recrystallization from methanol yielded white crystals, melting point 110°-112° C., yield 2.1 g.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 25 hours
  3. temperatureAfter cooling
  4. filtrationinorganic matter was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with water
  8. customdried
  9. customThe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=3:1)

Sources & evidence

ORD record
ord-0f5f7f9e8a774239b1fa7191e6a11c02
Source dataset
uspto-grants-1996_07
Patent number
US05538974

Reaction notes

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