Hydrochloric Acid → 2(1H)-Quinolinone, 3,4-dihydro-6-(3-(4-(2-ethoxyphenyl)-1-piperazinyl)propyl)-

HRID 1285456Notes

Reaction equation

HRID 1285456 reaction equation
Cl.O=[C:3]([C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26](=[O:31])[CH2:25][CH2:24]2)[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH2:19][CH3:20])[CH2:8][CH2:7]1.[H][H].Cl.[OH-].[Na+]>O.[Pd]>[CH2:19]([O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:9]1[CH2:10][CH2:11][N:6]([CH2:5][CH2:4][CH2:3][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[NH:27][C:26](=[O:31])[CH2:25][CH2:24]3)[CH2:7][CH2:8]1)[CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20229457HCID 20229457, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 30670912(1H)-Quinolinone, 3,4-dihydro-6-(3-(4-(2-ethoxyphenyl)-1-piperazinyl)propyl)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

2.0 Grams of 6-{1-oxo-3-[4-(2-ethoxyphenyl)-1-piperazinyl]propyl}-3,4-dihydrocarbostyril monohydrochloride and 0.4 g of palladium black were suspended in 100 ml of water and the suspension was catalytically hydrogenated under 3 atmospheric pressure of hydrogen gas at 80° C. Then 5 ml of concentrated hydrochloric acid was added to the reaction mixture and further catalytically hydrogenated. The catalyst was removed by filtration and to the filtrate thus obtained was neutralized by adding 10N-NaOH aqueous solution, then extracted with chloroform. The chloroform was removed by distillation and the residue thus obtained was purified by column chromatography. Recrystallized from ether to obtain 6-{3-[4-(2-ethoxyphenyl)-1-piperazinyl]propyl}-3,4-dihydrocarbostyril in colorless prism-like crystals. Yield: 0.8 g.

Workup

  1. customThe catalyst was removed by filtration and to the filtrate
  2. customthus obtained
  3. extractionextracted with chloroform
  4. customThe chloroform was removed by distillation
  5. customthe residue thus obtained
  6. customwas purified by column chromatography
  7. customRecrystallized from ether

Sources & evidence

ORD record
ord-a7ac8dc720e14c1e9c00e26476510058
Source dataset
uspto-grants-1986_01
Patent number
US04567187

Reaction notes

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