Potassium Iodide → HCID 13808657, compound

HRID 580079Notes

Reaction equation

HRID 580079 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[S:11][C:10]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:9]=2[O:8][CH2:7][CH:6]1[OH:18].[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>O.CN(C)C=O>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:9]2[O:8][CH2:7][C@@H:6]([OH:18])[C@@H:5]([CH2:4][CH2:3][CH2:2][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)[S:11][C:10]=2[CH:12]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 13808652HCID 13808652, compound

Product 1

HCID 13808657HCID 13808657, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(3-chloropropyl)-7-methoxy-3,4-dihydro-2H-1,5-benzoxathiepin-3-ol 500 mg, N-phenylpiperazine (500 mg), potassium iodide (50 mg), potassium carbonate (400 mg) and N,N-dimethylformamide (10 ml) is heated at 80° C. for 8 hours with stirring. The reaction mixture is poured into water, extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous sodium sulfate and evaporated to dryness in vacuo. The residue is submited to column chromatography on silica gel eluting with hexane-ethyl acetate-methanol (10:10:1) to give cis-7-methoxy-4-[3-(4-phenylpiperazin-1-yl)propyl]-3,4-dihydro-2H-1,5-benzoxathiepin-3-ol (colorless oil) which is isolated as the dihydrochloride (amorphous powder).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-761df0c36cd848a3adc6c3bd5edb3ea7
Source dataset
uspto-grants-1988_06
Patent number
US04751316

Reaction notes

Loading…