Sodium Thiosulfate → 6-(4-Acetoxypiperidino)-5-bromo-3,4-dihydrocarbostyril

HRID 487351Notes

Reaction equation

HRID 487351 reaction equation
[C:1]([O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16](=[O:21])[CH2:15][CH2:14]3)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[Br:22]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][C:20]=2[Br:22])[NH:17][C:16](=[O:21])[CH2:15][CH2:14]3)[CH2:9][CH2:10]1)(=[O:3])[CH3:2].[C:1]([O:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11]2[C:12]([Br:22])=[C:13]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16](=[O:21])[CH2:15][CH2:14]3)[CH2:9][CH2:10]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 190947246-(4-Acetoxypiperidino)-3,4-dihydrocarbostyril

Product 2

HCID 190947186-(4-Acetoxypiperidino)-5-bromo-3,4-dihydrocarbostyrilHCID 190947256-(4-Acetoxypiperidino)-7-bromo-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 300 mg of 6-(4-acetoxypiperidino)-3,4-dihydrocarbostyril in 7 ml of chloroform was added 370 mg of N-bromosuccinimide, and the mixture was stirred at room temperature for 1 hr. Then, an aqueous sodium thiosulfate was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was washed with brine, dried and evaporated under a reduced pressure. The crude mixture was purified by a silica gel column chromatography to give 87 mg of 6-(4-acetoxypiperidino)-7-bromo-3,4-dihydrocarbostyril and 41 mg of 6-(4-acetoxypiperidino)-5-bromo-3,4-dihydrocarbostyril.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with brine
  3. customdried
  4. customevaporated under a reduced pressure
  5. customThe crude mixture was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-6a4c00ab4b6745099a9539b782c4dfc4
Source dataset
uspto-grants-1994_03
Patent number
US05294718

Reaction notes

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