Water → HCID 22462568, compound

HRID 1936637Notes

Reaction equation

HRID 1936637 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][C:20]#[N:21])[CH2:15][CH:16]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])[CH2:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22462570HCID 22462570, compound

Product 1

HCID 22462568HCID 22462568, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-fluoro-3-[1-(3-cyanopropyl)-1,2,3,6-tetrahydropyridin-4-yl]indole (10 g, 35 mmol) in 300 ml of dry THF was added slowly LiAlH4 (2.0 g ). The mixture was stirred and heated to reflux for 2 h. Then the reaction mixture was cooled and water (1.9 ml) in THF (10 ml) was added slowly, followed by 2N sodium hydroxide (1.9 ml). This mixture was heated to reflux for 0.25 h , filtered over hyflo and concentrated to give 8.76 g (88%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. temperatureThen the reaction mixture was cooled
  4. temperatureThis mixture was heated
  5. temperatureto reflux for 0.25 h
  6. filtrationfiltered over hyflo
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a34df3a422834cb393c4659e3fb63c54
Source dataset
uspto-grants-2002_05
Patent number
US06391896B1

Reaction notes

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