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

HRID 1462552Notes

Reaction equation

HRID 1462552 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 separatedby 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. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-988cb0e9fdc04aff8e4764cd62bff13e
Source dataset
uspto-grants-1984_07
Patent number
US04460593

Reaction notes

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