Potassium Hydroxide → HCID 13324120, compound

HRID 2291169Notes

Reaction equation

HRID 2291169 reaction equation
O[C:2]1[CH:3]=[CH:4][C:5]([C:13](=[O:28])[CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[OH-].[K+].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>O.CN(C)C=O>[CH3:31][S:32]([C:2]1[CH:3]=[CH:4][C:5]([C:13](=[O:28])[CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2)(=[O:34])=[O:33]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 31297Methanesulfonyl chlorideHCID 13324119HCID 13324119, compound

Product 1

HCID 13324120HCID 13324120, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

37.9 Grams of 8-hydroxy-5-[1-oxo-3-(4-phenylpiperazinyl)propyl]-3,4-dihydrocarbostyril and 5.9 g of potassium hydroxide were dissolved in 400 ml of water and the solution was concentrated under a reduced pressure to obtain a residue. The residue was dissolved in 400 ml of dimethylformamide and then 12.0 g of methane-sulfonyl chloride was added dropwise to the solution under cooling condition. One hour after the addition either was added to the reaction mixture to obtain crystals. The crystals were collected by filtration and washed with acetone, then recrystallized from isopropanol to obtain 35.9 g of 8-methanesulfonyl-5-[1-oxo-3-(4-phenyl-1-piperazinyl)propyl]-3,4-dihydrocarbostyril in light brown needle-like crystal. Melting point: 165°-167° C.

Workup

  1. concentrationthe solution was concentrated under a reduced pressure
  2. customto obtain a residue
  3. temperatureunder cooling condition
  4. additionOne hour after the addition
  5. additionwas added to the reaction mixture
  6. customto obtain crystals
  7. filtrationThe crystals were collected by filtration
  8. washwashed with acetone
  9. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-cc0a243232524c25a10219e0add3f970
Source dataset
uspto-grants-1986_10
Patent number
US04619932

Reaction notes

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