Potassium Iodide → HCID 13536212, compound

HRID 1735729Notes

Reaction equation

HRID 1735729 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:20]([O:22][CH3:23])=[O:21])[S:12][C:11]2[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:10]=2[O:9][CH2:8][C:7]1=[O:19].[C:24]1([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:10]2[O:9][CH2:8][C:7](=[O:19])[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:33]3[CH2:34][CH2:35][N:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:31][CH2:32]3)([C:20]([O:22][CH3:23])=[O:21])[S:12][C:11]=2[CH:13]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 13808545HCID 13808545, compound

Product 1

HCID 13536212HCID 13536212, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 4-(4-bromobutyl)-7-methoxy-3-oxo-3,4-dihydro-2H-1,5-benzoxathiepine-4-carboxylate (1.7 g), N-phenylpiperazine (1.37 g), potassium iodide (0.7 g), anhydrous potassium carbonate (1.2 g) and acetonitrile (30 ml) was refluxed under heating for 1.5 hours. After cooling, inorganic matter was filtered off and the filtrate was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The organic layers were combined, 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=2:1) to give 1.0 g of colorless, oily methyl 7-methoxy-3-oxo-4-[4-(4-phenylpiperazin-1-yl)butyl]-3,4-dihydro-2H-1,5-benzoxathiepine-4-carboxylate. When converted to hydrochloride, a white powder was obtained, melting point 155°-165° C. (decomposition).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 1.5 hours
  3. temperatureAfter cooling
  4. filtrationinorganic matter was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionWater was added to the residue
  7. extractionthe mixture was extracted with ethyl acetate
  8. washwashed with water
  9. customdried
  10. customThe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=2:1)

Sources & evidence

ORD record
ord-88d281189ed4485a8e27ae8ffb3d6b51
Source dataset
uspto-grants-1996_07
Patent number
US05538974

Reaction notes

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