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

HRID 1979772Notes

Reaction equation

HRID 1979772 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([O:13][CH2:14][CH:15]3[O:17][CH2:16]3)[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4].[CH2:18]([CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CO.[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35].CC(C)=O>CC(C)=O>[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35].[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([O:13][CH2:14][CH:15]([OH:17])[CH2:16][N:28]3[CH2:29][CH2:30][CH:25]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:26][CH2:27]3)[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][C:3]1=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 317384-BenzylpiperidineHCID 129612621-Methyl-5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyrilHCID 88629647Oxalic acid acetone

Product 1

HCID 30610122(1h)-quinolinone, 3,4-dihydro-5-(2-hydroxy-3-(4-(phenylmethyl)-1-piperidinyl)propoxy)-1-methyl-, ethanedioate (1:1) (salt)Yield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.4 Grams of 1-methyl-5-(2,3-epoxypropoxy)-3,4-dihydrocarbostyril and 2.0 g of 4-benzylpiperidine were mixed with 30 ml of methanol and the mixture was heated under refluxing condition for 3 hours. The reaction mixture was concentrated under a reduced pressure and the residue thus obtained was dissolved in 30 ml of acetone and a 5%-oxalic acid-acetone solution was added under stirring at a room temperature to adjust the pH to 4.5 and allowed to stand. The precipitates thus formed were collected by filtration, washed with acetone and recrystallized from ethanol-ether to obtain 3.9 g (yield: 78%) of 1-methyl-5-[2-hydroxy-3-(4-benzyl-1-piperidyl)propoxy]-3,4-dihydrocarbostyril monooxalate as in the form of colorless powder. Melting point: 150°-152° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder refluxing condition for 3 hours
  3. concentrationThe reaction mixture was concentrated under a reduced pressure
  4. customthe residue thus obtained
  5. customThe precipitates thus
  6. customformed
  7. filtrationwere collected by filtration
  8. washwashed with acetone
  9. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-f5cd2924a5f34f9fa8248c2f177ef49c
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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