Potassium Iodide → HCID 13536203, compound

HRID 652436Notes

Reaction equation

HRID 652436 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 10 g of methyl 7-methoxy-3-oxo-3,4-dihydro-2H-1,5-benzoxathiepin-4-carboxylate, 9.8 g of 3-(4-phenylpiperazin-1-yl)propyl chloride, 6.2 g of anhydrous potassium carbonate, 3.0 g of potassium iodide and 150 ml of methyl ethyl ketone is stirred with heating under reflux for 25 hours. After the mixture is cooled, the inorganic substance is filtered off, and the filtrate is concentrated under reduced pressure. The resulting residue is dissolved in ethyl acetate, and the solution is washed with water and dried. The solvent is evaporated off under reduced pressure, and the resulting residue is purified by column chromatography on silica gel (eluent: hexane:ethyl acetate =3:1) to give methyl 7-methoxy-3-oxo-4-[3-(4-phenylpiperazin-1-yl)propyl]-3,4-dihydro-2H-1,5-benzoxathiepin-4-carboxylate. Recrystallization from methanol gives white crystals. m.p. of 110°-112° C. Yield of 2.1 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 25 hours
  3. temperatureAfter the mixture is cooled
  4. filtrationthe inorganic substance is filtered off
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. dissolutionThe resulting residue is dissolved in ethyl acetate
  7. washthe solution is washed with water
  8. customdried
  9. customThe solvent is evaporated off under reduced pressure
  10. customthe resulting residue is purified by column chromatography on silica gel (eluent: hexane:ethyl acetate =3:1)

Sources & evidence

ORD record
ord-9818f37bd33842f9b309db7a89ed0d76
Source dataset
uspto-grants-1987_06
Patent number
US04672064

Reaction notes

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