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

HRID 1790448Notes

Reaction equation

HRID 1790448 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][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]([CH:23]=[N:24]O)[CH:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:27]=[CH:26][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][NH2:24])[CH:21]=4)[CH2:16][CH2:15]3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 734445891-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindoline

Product 1

HCID 220380351-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice cooling and stirring, 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindoline (31 g) was added in portions to a suspension of lithium aluminum hydride (8.0 g) in tetrahydrofuran (500 ml) and then the resultant mixture was heated under reflux for 3 hr. Under cooling with ice water, water (8 ml), a 5 N aqueous solution (24 ml) of sodium hydroxide and further water (8 ml) were carefully added dropwise to the reaction solution followed by vigorous stirring. The resulting precipitate was filtered off and the filtrate was concentrated under reduced pressure to give the crude title compound (about 30 g). A portion of this crude product was purified by NH-silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate-isopropyl ether mixtures to give the title compound as a pale yellow powder.

Workup

  1. temperatureunder reflux for 3 hr
  2. filtrationThe resulting precipitate was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give the crude title compound (about 30 g)
  5. customA portion of this crude product was purified by NH-silica gel column chromatography (ethyl acetate)
  6. customrecrystallized from ethyl acetate-isopropyl ether mixtures

Sources & evidence

ORD record
ord-f67998969c9543d6b23fd1c0c58706c3
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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