Hydrochloric Acid → 2(1H)-Quinolinone, 4-phenyl-7-(3-(4-phenyl-1-piperidinyl)propoxy)-, monohydrochloride

HRID 1979773Notes

Reaction equation

HRID 1979773 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[OH-].[K+].[Cl:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:27][CH2:26]1.C(=O)([O-])O.[Na+].Cl>CO.CN(C)C=O>[ClH:21].[C:13]1([C:6]2[C:5]3[C:10](=[CH:11][C:2]([O:1][CH2:22][CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][CH:28]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH2:29][CH2:30]4)=[CH:3][CH:4]=3)[NH:9][C:8](=[O:12])[CH:7]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 2036891-(3-Chloropropyl)-4-phenylpiperidineHCID 516892Sodium BicarbonateHCID 13363012HCID 13363012, compound

Product 1

HCID 30610082(1H)-Quinolinone, 4-phenyl-7-(3-(4-phenyl-1-piperidinyl)propoxy)-, monohydrochlorideYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

2.4 Grams of 7-hydroxy-4-phenylcarbostyril and 0.8 g of potassium hydroxide were mixed with 60 ml of methanol and concentrated under a reduced pressure to dryness. To the residue thus obtained was added 60 ml of dimethylformamide and well mixed, then 5 g of 1-(3-chloropropyl)-4-phenylpiperidine was added to the mixture and heated at 70°-80° C. for 8 hours under stir ring condition. The reaction mixture was concentrated under a reduced pressure to dryness, and to the residue thus obtained was added 60 ml of 5% sodium hydrogen-carbonate aqueous solution and extracted with chloroform. The chloroform layer was washed with water, dried and the chloroform was removed by distillation. To the residue thus obtained was added 30 ml of methanol and 5 ml of concentrated hydrochloric acid, and concentrated under a reduced pressure. The residue was crystallized with ethanol then recrystallized from methanol to obtain 2.8 g (58%) of 4-phenyl-7-[3-(4-phenyl-1-piperidyl)propoxy]carbostyril monohydrochloride as in the form of colorless needle-like crystals. Melting point: 238°-241° C.

Workup

  1. concentrationconcentrated under a reduced pressure to dryness
  2. customTo the residue thus obtained
  3. additionwell mixed
  4. temperatureheated at 70°-80° C. for 8 hours
  5. concentrationThe reaction mixture was concentrated under a reduced pressure to dryness
  6. customto the residue thus obtained
  7. extractionextracted with chloroform
  8. washThe chloroform layer was washed with water
  9. customdried
  10. customthe chloroform was removed by distillation
  11. customTo the residue thus obtained
  12. concentrationconcentrated under a reduced pressure
  13. customThe residue was crystallized with ethanol
  14. customthen recrystallized from methanol

Sources & evidence

ORD record
ord-2a79f59bc5544a45ba0687842e927475
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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