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

HRID 1462552노트

반응식

HRID 1462552 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-988cb0e9fdc04aff8e4764cd62bff13e
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04460593

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