Sodium Iodide → HCID 13084716, compound

HRID 1285452Notes

Reaction equation

HRID 1285452 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2.[I-].[Na+].[CH3:19][N:20]([CH3:23])[CH:21]=O.C(=O)([O-])O.[Na+]>CC(C)=O>[C:6]1([CH3:7])[CH:15]=[CH:14][C:19]([N:20]2[CH2:23][CH2:13][N:12]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]3[CH:7]=[C:8]4[C:13](=[CH:14][CH:15]=3)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]4)[CH2:11][CH2:21]2)=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 13084735HCID 13084735, compound

Product 1

HCID 13084716HCID 13084716, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

2.5 Grams of 6-(4-chlorobutyl)-3,4-dihydrocarbostyril and 1.8 g of sodium iodide were mixed in 80 ml of acetone and stirred at 50° C. for 2 hours. Then to the reaction mixture was added 80 ml of dimethylformamide and the acetone was removed by distillation, and 2.0 g of 4-(4-tolyl)piperazine and 2.0 g of triethylamine were added to the reaction mixture, and stirred at 70°-80° C. for 5 hours. The reaction mixture was concentrated under a reduced pressure to obtain a residue. To the residue was added 50 ml of 5%-sodium hydrogencarbonate aqueous solution and stirred. The precipitates thus formed were collected by filtration, washed with water and dried. Recrystallization from isopropanol-diisopropyl ether, there were obtained 3.1 g of 6-{4-[4-(4-tolyl)-1-piperazinyl]butyl}-3,4-dihydrocarbostyril in colorless prism-like crystals, having the melting point of 160°-161° C.

Workup

  1. customthe acetone was removed by distillation, and 2.0 g of 4-(4-tolyl)piperazine and 2.0 g of triethylamine
  2. additionwere added to the reaction mixture
  3. stirringstirred at 70°-80° C. for 5 hours
  4. concentrationThe reaction mixture was concentrated under a reduced pressure
  5. customto obtain a residue
  6. stirringstirred
  7. customThe precipitates thus
  8. customformed
  9. filtrationwere collected by filtration
  10. washwashed with water
  11. customdried
  12. customRecrystallization from isopropanol-diisopropyl ether

Sources & evidence

ORD record
ord-aa5e7732235245f29a7bab7005fda04e
Source dataset
uspto-grants-1986_01
Patent number
US04567187

Reaction notes

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