1-[1-(2-Fluorophenethyl)piperidin-4-yl]-6-formylindoline → 1-[1-(2-Fluorophenethyl)piperidin-4-yl]-6-formylindole

HRID 1790506Notes

Reaction equation

HRID 1790506 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=[O:22])[CH:19]=3)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=[O:22])[CH:19]=3)[CH:14]=[CH:13]2)[CH2:10][CH2:11]1

Participants

4

Reactant 1

HCID 220379081-[1-(2-Fluorophenethyl)piperidin-4-yl]-6-formylindoline

Product 1

HCID 220383201-[1-(2-Fluorophenethyl)piperidin-4-yl]-6-formylindoleYield 78%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6212ChloroformSolvent

Procedure

A suspension of 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-formylindoline (2.50 g) obtained in Example 348-3) and activated manganese dioxide (5.0 g) in chloroform (100 ml) was heated under reflux for 4 hr under vigorous stirring. Further, activated manganese dioxide (5.0 g×1, 2.5 g×2) was added to the reaction mixture at 1 hr intervals and the resultant mixture was reacted for additional 2 hr. The reaction solution was filtered through celite and the residue was washed with chloroform. The filtrate was concentrated under reduced pressure to give the title compound (1.94 g) as a yellow powder (yield: 78.0%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hr under vigorous stirring
  3. filtrationThe reaction solution was filtered through celite
  4. washthe residue was washed with chloroform
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3ebb3a470de94017a092fdbf3885cf0a
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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