HCID 19030945, compound → HCID 19030928, compound

HRID 266830Notes

Reaction equation

HRID 266830 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH2:7]([S:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:38]=[CH:37][C:17]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:30][CH2:29][C:27]3=[O:28])[CH2:22][CH2:21]2)=[O:19])=[CH:16][CH:15]=1)[CH3:8]>O.CO>[CH2:7]([S:9]([CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:38]=[CH:37][C:17]([C:18]([N:20]2[CH2:21][CH2:22][CH:23]([N:26]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH2:30][CH2:29][C:27]3=[O:28])[CH2:24][CH2:25]2)=[O:19])=[CH:16][CH:15]=1)=[O:2])[CH3:8]

Participants

5

Reactant 2

HCID 19030945HCID 19030945, compoundHCID 23667635Sodium periodate

Product 1

HCID 19030928HCID 19030928, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium metaperiodate (0.28 g) is dissolved in water (4 ml) and thereto is added a solution of 1-{1-[4-(3-ethylthiopropoxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (0.4 g) in methanol (15 ml) and the mixture is stirred at room temperature overnight. The reaction mixture is concentrated and the residue is extracted with chloroform. The extract is dried with magnesium sulfate and the solvent is distilled off. The resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:2→ethyl acetate:methanol=20:1) to give 1-{1-[4-(3-ethylsulfinylpropoxy)benzoyl]-4-piperidinyl]-3,4-dihydrocarbostyril (0.12 g).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. extractionthe residue is extracted with chloroform
  3. dry with materialThe extract is dried with magnesium sulfate
  4. distillationthe solvent is distilled off
  5. customThe resulting residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:2→ethyl acetate:methanol=20:1)

Sources & evidence

ORD record
ord-9cdfa6c91e4a407e8ac4ced0b1b25345
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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