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

HRID 1790508Notes

Reaction equation

HRID 1790508 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][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]=NO)[CH:19]=3)[CH:14]=[CH:13]2)[CH2:8][CH2:7]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH2:34].[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][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:34])[CH:19]=3)[CH:14]=[CH:13]2)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 865844061-[1-(2-Fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindole

Product 1

HCID 220383201-[1-(2-Fluorophenethyl)piperidin-4-yl]-6-formylindoleYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindole (1.95 g) in tetrahydrofuran (50 ml) was added dropwise at room temperature under ice cooling and stirring into a suspension of lithium aluminum hydride (0.4 g) in tetrahydrofuran (100 ml). Then the resultant mixture was heated under reflux for 3 hr. Under ice watar cooling, water (1 ml), a 5 N aqueous solution of sodium hydroxide (3 ml) and further water (1 ml) were carefully added dropwise into the reaction mixtures and the mixture was further vigorously stirred. The resulting precipitate was collected by filtration and washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography (ethyl acetate) to give the title compound (0.92 g) as a brown wax (yield: 49.1%).

Workup

  1. temperatureunder reflux for 3 hr
  2. temperatureUnder ice watar cooling
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with tetrahydrofuran
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by NH-silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-07b3222edee24a299a40596e3bee1cb6
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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