Aluminium lithium hydride → HCID 59831919, compound

HRID 268756Notes

Reaction equation

HRID 268756 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][C:12]#[N:13])[CH:8]=2)[CH:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][CH2:12][NH2:13])[CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59831860HCID 59831860, compound

Product 1

HCID 59831919HCID 59831919, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 3-(1H-indol-6-yl)-3-phenyl-propionitrile XIII (1.1 g, 4.5 mmol) in THF (35 ml) was slowly added a suspension of LiAlH4 (0.51 g, 13 mmol) in THF (10 ml). The mixture was stirred 10 min at 0° C. and 10 minutes at room temperature, then it was refluxed for 1.5 hours. The reaction mixture was cooled to 0° C., quenched by the careful addition of freshly ground Na2SO4.10H2O (25 g), filtered, and the solid was washed with EtOAc. The filtrate was concentrated and purified via flash chromatography (DCM/MeOH/NH4OH) affording 3-(1H-indol-6-yl)-3-phenyl-propylamine XIV as a colorless oil (0.68 g, 62% yield).

Workup

  1. temperatureit was refluxed for 1.5 hours
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched by the careful addition of freshly ground Na2SO4.10H2O (25 g)
  4. filtrationfiltered
  5. washthe solid was washed with EtOAc
  6. concentrationThe filtrate was concentrated
  7. custompurified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-1ea6fa7df8de40e992daa264d41fe65d
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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