4-Benzylpiperidine → 2(1H)-Quinolinone, 3,4-dihydro-1-methyl-7-(3-(4-(phenylmethyl)-1-piperidinyl)propoxy)-, ethanedioate (1:1)

HRID 1979768Notes

Reaction equation

HRID 1979768 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:14][CH2:15][CH2:16]Cl)[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.C(=O)([O-])O.[Na+].CC(C)=O.[C:40]([OH:45])(=[O:44])[C:41]([OH:43])=[O:42]>CC(C)=O.CN(C)C=O.C(N(CC)CC)C>[C:40]([OH:45])(=[O:44])[C:41]([OH:43])=[O:42].[CH3:1][N:2]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:14][CH2:15][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:11]=2)[CH2:6][CH2:5][C:3]1=[O:4]

Participants

8

Reactant 4

HCID 317384-BenzylpiperidineHCID 516892Sodium BicarbonateHCID 204385571-Methyl-7-(3-chloropropoxy)-3,4-dihydrocarbostyrilHCID 88629647Oxalic acid acetone

Product 1

HCID 30609872(1H)-Quinolinone, 3,4-dihydro-1-methyl-7-(3-(4-(phenylmethyl)-1-piperidinyl)propoxy)-, ethanedioate (1:1)Yield 86%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

4.9 Grams of 1-methyl-7-(3-chloropropoxy)-3,4-dihydrocarbostyril, 4.2 g of 4-benzylpiperidine and 3 g of triethylamine were mixed with 60 ml of dimethylformamide. The mixture was heated at 70°-80° C. for 8 hours. After the reaction was completed, the reaction mixture was concentrated under a reduced pressure to dryness. To the residue thus obtained was added 5%-sodium hydrogencarbonate aqueous solution and extracted with chloroform. The chloroform layer was washed with water and dried, then chloroform was removed by distillation. The residue thus obtained was dissolved in 30 ml of acetone, and under stirring condition a 5%-oxalic acid acetone solution was added thereto to make pH 4.5 then was allowed to stand. Precipitates thus formed were obtained by filtration, washed with acetone, then recrystallized from ethanol-ether to obtain 7.9 g (yield: 86%) of 1-methyl-7-[3-(4-benzyl-1-piperidyl)propoxy]-3,4-dihydrocarbostyril monooxalate as in the form of colorless powder. Melting point: 175°-177° C.

Workup

  1. temperatureThe mixture was heated at 70°-80° C. for 8 hours
  2. concentrationthe reaction mixture was concentrated under a reduced pressure to dryness
  3. customTo the residue thus obtained
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water
  6. customdried
  7. customchloroform was removed by distillation
  8. customThe residue thus obtained
  9. additionwas added
  10. customPrecipitates thus
  11. customformed
  12. customwere obtained by filtration
  13. washwashed with acetone
  14. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-8fe847a5004a459cb819cb3142cd1b17
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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