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 1979771Notes

Reaction equation

HRID 1979771 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3cb4e3e5d75b4624b3d218e6816b9753
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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