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 1979771ノート

反応式

HRID 1979771 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3cb4e3e5d75b4624b3d218e6816b9753
出典データセット
uspto-grants-1984_11
特許番号
US04482560

反応ノート

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