Acetone → 6-(3-(4-(3-Methylphenyl)-1-piperazinyl)-1-propenyl)-3,4-dihydro-2(1H)-quinolinone

HRID 2291193Notes

Reaction equation

HRID 2291193 reaction equation
O=[C:2]([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[CH2:22][CH2:21]2)[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[C:13]([CH3:17])[CH:14]=[CH:15][CH:16]=2)[CH2:7][CH2:6]1.[BH4-].[Na+].CC(C)=O.[OH-].[Na+]>CO.CCOCC>[C:13]1([CH3:17])[CH:14]=[CH:15][CH:16]=[C:11]([N:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH:3]=[CH:2][C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23](=[O:28])[CH2:22][CH2:21]4)[CH2:6][CH2:7]2)[CH:12]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 20229462HCID 20229462, compound

Product 1

HCID 30670856-(3-(4-(3-Methylphenyl)-1-piperazinyl)-1-propenyl)-3,4-dihydro-2(1H)-quinolinone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

5.0 Grams of 6-{1-oxo-3-[4-(3-tolyl)-1-piperazinyl]-propyl]-3,4-dihydrocarbostyril was suspended in 250 ml of methanol, and 2.5 g of sodium borohydride was added gradually to this solution under ice-cooling condition and the mixture was stirred for 30 minutes. Then 10 ml of acetone was added to the mixture and the reaction mixture was concentrated under a reduced pressure to dryness. To the residue thus obtained were added 10N-NaOH and ether and stirred at a room temperature for 30 minutes. The crystals thus formed were collected by filtration and were suspended in 250 ml of dioxane then added 10 ml of concentrated hydrochloric acid. The mixture was refluxed for 15 minutes then concentrated under a reduced pressure to dryness. The residue thus obtained was separated by a silica-gel chromatography and recrystallized from ethanol to obtain 6-{3-[4-(3-tolyl)-1-piperazinyl]-1-propenyl}-3,4-dihydrocarbostyril in colorless prism-like crystals. Yield: 2.9 g

Workup

  1. temperaturecooling condition
  2. concentrationthe reaction mixture was concentrated under a reduced pressure to dryness
  3. customTo the residue thus obtained
  4. stirringstirred at a room temperature for 30 minutes
  5. customThe crystals thus formed
  6. filtrationwere collected by filtration
  7. additionthen added 10 ml of concentrated hydrochloric acid
  8. temperatureThe mixture was refluxed for 15 minutes
  9. concentrationthen concentrated under a reduced pressure to dryness
  10. customThe residue thus obtained
  11. customwas separated by a silica-gel chromatography
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-1fb6d25d3e82415b82a220c8e1cdc102
Source dataset
uspto-grants-1986_10
Patent number
US04619932

Reaction notes

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