4-Benzylpiperidine → 2(1h)-quinolinone, 3,4-dihydro-5-(2-hydroxy-3-(4-(phenylmethyl)-1-piperidinyl)propoxy)-1-(2-propenyl)-, ethanedioate (1:1) (salt)

HRID 1979771노트

반응식

HRID 1979771 반응식
[CH2:1]([N:4]1[C:14]2[C:9](=[C:10]([O:15][CH2:16][CH:17]([OH:20])[CH2:18]Cl)[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:5]1=[O:6])[CH:2]=[CH2:3].[CH2:21]([CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+].CC(C)=O.[C:43]([OH:48])(=[O:47])[C:44]([OH:46])=[O:45]>CC(C)=O.CN(C)C=O.C(N(CC)CC)C>[C:43]([OH:48])(=[O:47])[C:44]([OH:46])=[O:45].[CH2:1]([N:4]1[C:14]2[C:9](=[C:10]([O:15][CH2:16][CH:17]([OH:20])[CH2:18][N:31]3[CH2:32][CH2:33][CH:28]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:29][CH2:30]3)[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:5]1=[O:6])[CH:2]=[CH2:3]

참가 물질

8

반응물 4

HCID 317384-BenzylpiperidineHCID 516892Sodium BicarbonateHCID 129612711-Allyl-5-(2-hydroxy-3-chloropropoxy)-3,4-dihydrocarbostyrilHCID 88629647Oxalic acid acetone

생성물 1

HCID 30609942(1h)-quinolinone, 3,4-dihydro-5-(2-hydroxy-3-(4-(phenylmethyl)-1-piperidinyl)propoxy)-1-(2-propenyl)-, ethanedioate (1:1) (salt)수율 82%

시약·촉매·용매 3

HCID 180Acetone용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

2.6 Grams of 1-allyl-5-(2-hydroxy-3-chloropropoxy)-3,4-dihydrocarbostyril, 1.5 g of triethylamine and 2.0 g of 4-benzylpiperidine were mixed with 30 ml of dimethylformamide and the mixture was stirred at 80°-90° C. for 5 hours. The reaction mixture was poured into 80 ml of a 5%-sodium hydrogencarbonate aqueous solution and the organic layer was extracted with chloroform, and the chloroform layer was washed with water and dried. Then the chloroform was removed by distillation and the residue thus obtained was dissolved in 30 ml of acetone and further 5%-oxalic acid acetone solution was added to make the pH to 4.5 and the crystals formed were collected by filtration and washed with acetone. Recrystallization from ethanol to obtain 4.3 g (yield: 82%) of 1-allyl-5-[2-hydroxy-(4-benzyl-1-piperidyl)propoxy]-3,4-dihydrocarbostyril monooxalate as in the form of colorless needle-like crystals. Melting point: 178°-180° C.

후처리

  1. extractionthe organic layer was extracted with chloroform
  2. washthe chloroform layer was washed with water
  3. customdried
  4. customThen the chloroform was removed by distillation
  5. customthe residue thus obtained
  6. customthe crystals formed
  7. filtrationwere collected by filtration
  8. washwashed with acetone
  9. customRecrystallization from ethanol

출처 및 근거

ORD 기록
ord-3cb4e3e5d75b4624b3d218e6816b9753
출처 데이터셋
uspto-grants-1984_11
특허 번호
US04482560

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