Water → 8-{3-[4-(2-Methoxyphenyl)-1-piperazinyl]-propoxycarbonyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran dihydrochloride

HRID 2259895Notes

Reaction equation

HRID 2259895 reaction equation
[C:1]([C:4]1[C:13]2[O:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:10]([CH3:20])[C:9](=[O:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([OH:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[Cl:28][CH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][N:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[O:44][CH3:45])[CH2:34][CH2:33]1.O>CN(C)C=O>[ClH:28].[ClH:28].[CH3:45][O:44][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=1[N:35]1[CH2:34][CH2:33][N:32]([CH2:31][CH2:30][CH2:29][O:2][C:1]([C:4]2[C:13]3[O:12][C:11]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)=[C:10]([CH3:20])[C:9](=[O:21])[C:8]=3[CH:7]=[CH:6][CH:5]=2)=[O:3])[CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 770163-Methylflavone-8-carboxylic acidHCID 6226691-(3-Chloropropyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 199725188-{3-[4-(2-Methoxyphenyl)-1-piperazinyl]-propoxycarbonyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran dihydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4.24 g of 8-carboxy-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran and 6.3 g of anhydrous potassium carbonate in 60 ml of dimethylformamide was stirred at 80° C. for 30 minutes. 5.23 g of 1-(3-chloropropyl)-4-(2-methoxyphenyl)-piperazine was then added and stirring was continued at 80° C. for 3.5 hours. The reaction mixture was cooled to ambient temperature, poured on to iced water and extracted with ethyl acetate. The organic extracts were washed with aqueous sodium chloride solution, dried on anhydrous sodium sulfate, and evaporated to dryness in vacuo. The residue was taken up in ethanol and excess ethanolic hydrogen chloride was added to the solution. Yield: 8.16 g of the title compound, m.p. 198°-203° C.

Workup

  1. stirringstirring
  2. waitwas continued at 80° C. for 3.5 hours
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic extracts were washed with aqueous sodium chloride solution
  6. dry with materialdried on anhydrous sodium sulfate
  7. customevaporated to dryness in vacuo
  8. additionexcess ethanolic hydrogen chloride was added to the solution

Sources & evidence

ORD record
ord-06b52a01f18740e4bac24a8d11c686f6
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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