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

HRID 2259896Notes

Reaction equation

HRID 2259896 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][O:25][C:26]([C:28]1[C:37]2[O:36][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[C:34]([CH3:44])[C:33](=[O:45])[C:32]=2[CH:31]=[CH:30][CH:29]=1)=[O:27].O>CN(C)C=O>[ClH:2].[ClH:1].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:22][CH2:23][CH2:24][O:25][C:26]([C:28]2[C:37]3[O:36][C:35]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[C:34]([CH3:44])[C:33](=[O:45])[C:32]=3[CH:31]=[CH:30][CH:29]=2)=[O:27])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 30170151-(2-Chlorophenyl)piperazinium chlorideHCID 199726458-(3-bromopropoxycarbonyl)-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran

Product 1

HCID 199726198-{3-[4-(2-Chlorophenyl)-1-piperazinyl]-propoxycarbonyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran dihydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.8 g of 1-(2-chlorophenyl)-piperazine hydrochloride and 4.2 g of anhydrous potassium carbonate in 25 ml of dimethylformamide was stirred at ambient temperature for 15 minutes. 4.81 g of Intermediate I was added, and stirring was continued for 2 days. The reaction mixture was then poured into 200 ml of cold water, and extracted with diethyl ether and ethyl acetate. The organic extracts were washed in turn with aqueous sodium chloride solution, 0.1N aqueous acetic acid solution, aqueous sodium chloride solution, aqueous 4% sodium carbonate solution and water, and were then dried on anhydrous sodium sulfate. After evaporation to dryness in vacuo, the residue was dissolved in 160 ml of acetonitrile and excess hydrogen chloride in diethyl ether was added. The insoluble title compound was recrystallized from acetonitrile. Yield 3.6 g, m.p. 138°-143° C.

Workup

  1. stirringstirring
  2. waitwas continued for 2 days
  3. extractionextracted with diethyl ether and ethyl acetate
  4. washThe organic extracts were washed in turn with aqueous sodium chloride solution, 0.1N aqueous acetic acid solution, aqueous sodium chloride solution, aqueous 4% sodium carbonate solution and water
  5. dry with materialwere then dried on anhydrous sodium sulfate
  6. customAfter evaporation to dryness in vacuo
  7. dissolutionthe residue was dissolved in 160 ml of acetonitrile
  8. additionexcess hydrogen chloride in diethyl ether was added
  9. customThe insoluble title compound was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d34b79cdb54a4a31bf87072683729f87
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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