Hydrochloric Acid → HCID 86749652, compound

HRID 1735734Notes

Reaction equation

HRID 1735734 reaction equation
[Cl:1][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+].[ClH:39]>O.CN(C)C=O>[ClH:1].[ClH:39].[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

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 13808652HCID 13808652, compound

Product 1

HCID 86749652HCID 86749652, 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) was stirred at 80° C for 8 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexaneethyl acetate-methanol=10:10:1), and a colorless oil obtained was converted to hydrochloride and recrystallized from methanol-acetone to give a white powder of cis 7-methoxy-4-[3(4-phenylpiperazin-1-yl)propyl]-3,4-dihydro-2H-1,5-benzoxathiepin-3-ol dihydrochloride obtained in Reference Example 26.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexaneethyl acetate-methanol=10:10:1)
  6. customa colorless oil obtained
  7. customrecrystallized from methanol-acetone

Sources & evidence

ORD record
ord-16684eed67b54afab7da92ecf4dc26dc
Source dataset
uspto-grants-1996_07
Patent number
US05538974

Reaction notes

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