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

HRID 1462539Notes

Reaction equation

HRID 1462539 reaction equation
[O:1]=[C:2]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24](=[O:29])[CH2:23][CH2:22]2)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[CH2:8][CH2:7]1.[BH4-].[Na+].Cl>CO>[OH:1][CH:2]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24](=[O:29])[CH2:23][CH2:22]2)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 130648276-{1-Oxo-4-[4-(3-chlorophenyl)-1-piperazinyl]butyl}-3,4-dihydrocarbostyril

Product 1

HCID 30670792(1H)-Quinolinone, 3,4-dihydro-6-(4-(4-(3-chlorophenyl)-1-piperazinyl)-1-hydroxybutyl)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.0 Grams of 6-{1-oxo-4-[4-(3-chlorophenyl)-1-piperazinyl]butyl}-3,4-dihydrocarbostyril was added to 100 ml of methanol, under stirring condition 1.2 g of sodium borohydride was added gradually to the solution and stirred at a room temperature for 5 hours. Then 5 ml of concentrated hydrochloric acid was added to the reaction mixture and the mixture was concentrated under a reduced pressure to dryness. Then to this dried matter was added 50 ml of 2%-sodium hydroxide aqueous solution and the organic layer was extracted with dichloromethane. The dichloromethane layer was washed with water, dried and the dichloromethane was removed by distillation. The residue thus obtained was purified by a silica gel column chromatography, and recrystallized from isopropanol to obtain 2.2 g of 6-{1-hydroxy-4[4-(3-chlorophenyl)-1-piperazinyl]butyl}-3,4-dihydrocarbostyril in colorless needle-like crystals.

Workup

  1. additionwas added gradually to the solution
  2. concentrationthe mixture was concentrated under a reduced pressure to dryness
  3. additionThen to this dried matter was added 50 ml of 2%-sodium hydroxide aqueous solution
  4. extractionthe organic layer was extracted with dichloromethane
  5. washThe dichloromethane layer was washed with water
  6. customdried
  7. customthe dichloromethane was removed by distillation
  8. customThe residue thus obtained
  9. customwas purified by a silica gel column chromatography
  10. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-d4896971cc1b41e99b8f5e142baedfff
Source dataset
uspto-grants-1984_07
Patent number
US04460593

Reaction notes

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