HCID 19030945, compound → HCID 19030928, compound

HRID 1708305Notes

Reaction equation

HRID 1708305 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-fe55fe4302d94b10bc4a359d534a2e1e
Source dataset
uspto-grants-1994_10
Patent number
US05356904

Reaction notes

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