Aluminium lithium hydride → 4-(8-Azabicyclo[3.2.1]oct-8-yl)-3-fluorobenzylamine

HRID 586070Notes

Reaction equation

HRID 586070 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]12[N:14]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=3[F:23])[CH:11]([CH2:12][CH2:13]1)[CH2:10][CH2:9][CH2:8]2>C1COCC1>[CH:11]12[N:14]([C:15]3[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][C:16]=3[F:23])[CH:7]([CH2:13][CH2:12]1)[CH2:8][CH2:9][CH2:10]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 223376114-(8-Azabicyclo[3.2.1]oct-8-yl)-3-fluorobenzonitrile

Product 1

HCID 223376704-(8-Azabicyclo[3.2.1]oct-8-yl)-3-fluorobenzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1.6 g; 43.2 mmol) in THF was treated with 4-(8-azabicyclo[3.2.1]oct-8-yl)-3-fluorobenzonitrile (2.48 g; 10.8 mmol) dropwise. After complete addition, the slurry was refluxed for 2 hours, allowed to cool to ambient temperature, and quenched with sodium sulfate decahydrate. The mixture was filtered and the filter cake was washed with THF (2×50 mL). The organics were combined and concentrated under reduced pressure. The residue was chromatographed (SiO2; 5% methanol in methylene chloride) to provide the title compound. 1H NMR (DMSO-d6) δ 7.03 (dd, 1H), 7.92 (dd, 1H), 7.85 (t, 1H), 4.21 (s, 2H), 3.60 (s, 2H), 1.93 (m, 2H), 1.77 (m, 5H), 1.42 (m, 1H), 1.32 (m, 2H); MS (ESI) m/z 235, (M+H)+.

Workup

  1. additionAfter complete addition
  2. temperaturethe slurry was refluxed for 2 hours
  3. customquenched with sodium sulfate decahydrate
  4. filtrationThe mixture was filtered
  5. washthe filter cake was washed with THF (2×50 mL)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed (SiO2; 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-0a93bfd90536436f81b1b2f9e02ee431
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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