Sodium Iodide → HCID 20249003, compound

HRID 1462526Notes

Reaction equation

HRID 1462526 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:14](=[O:18])[CH2:15][CH2:16]Cl)=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9][CH2:8]2.[I-].[Na+].[C:21]1([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.CCOCC.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:14](=[O:18])[CH2:15][CH2:16][N:30]2[CH2:31][CH2:32][N:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:28][CH2:29]2)=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9][CH2:8]2

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 70961-PhenylpiperazineHCID 516892Sodium BicarbonateHCID 20229426HCID 20229426, compound

Product 1

HCID 20249003HCID 20249003, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

26.8 Grams of 8-methoxy-5-(3-chloropropionyl)-3,4-dihydrocarbostyril and 16.5 g of sodium iodide were dissolved in 200 ml of dimethylformamide and the mixture was stirred at 40° C. for 1 hour. Then 11.1 g triethyl amine and 17.1 g of 4-phenylpiperazine were added to the mixture and stirred at 40° C. for 2 hours additionally. The reaction mixture was concentrated under a reduced pressure to obtain a residue. Then a 5%-sodium hydrogencarbonate aqueous solution and ether were added to the residue to obtain crystalline precipitates. The precipitates were collected by filtration and were recrystallized from ethanol to obtain 8-methoxy-5-[1-oxo-3-(4-phenyl-1-piperazinyl)propyl]-3,4-dihydrocarbostyril. Yield: 27.5 g.

Workup

  1. stirringstirred at 40° C. for 2 hours additionally
  2. concentrationThe reaction mixture was concentrated under a reduced pressure
  3. customto obtain a residue
  4. customto obtain crystalline precipitates
  5. filtrationThe precipitates were collected by filtration
  6. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-4168128ab4974cf28b75bab12c8f4a27
Source dataset
uspto-grants-1984_07
Patent number
US04460593

Reaction notes

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