1-(4-Fluorophenethylpiperdin-4-yl]-6-acetamidomethylindoline → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindole

HRID 1790493Notes

Reaction equation

HRID 1790493 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[CH:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>CC(C)=O.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[CH:21]=4)[CH:16]=[CH:15]3)[CH2:12][CH2:13]2)=[CH:28][CH:29]=1

Participants

4

Reactant 1

HCID 100007861-(4-Fluorophenethylpiperdin-4-yl]-6-acetamidomethylindoline

Product 1

HCID 98435371-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindoleYield 56.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindoline (7.5 g) obtained in Example 133 was dissolved in acetone (500 ml) at 50° C. To the resultant solution was added active manganese dioxide (35.6 g) in portions under stirring. The resulting suspension was heated under reflux for 1.5 hr, then filtered through celite and washed with acetone. The filtrate was concentrated under reduced pressure and the resulting pale yellow solid was recrystallized from ethyl acetate to give the title compound (4.2 g) as awhite powder (yield: 56%).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureunder reflux for 1.5 hr
  3. filtrationfiltered through celite
  4. washwashed with acetone
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting pale yellow solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e0463063f5d14fa394ec031932afb9ba
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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