Aluminium lithium hydride → HCID 22605564, compound

HRID 2307435Notes

Reaction equation

HRID 2307435 reaction equation
[N:1]([CH:4]([C:6]1[CH:7]=[CH:8][C:9]([F:18])=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:11]=1)[CH3:5])=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:18][C:9]1[CH:8]=[CH:7][C:6]([CH:4]([NH2:1])[CH3:5])=[CH:11][C:10]=1[N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22605624HCID 22605624, compound

Product 1

HCID 22605564HCID 22605564, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[5-(1-azido-ethyl)-2-fluoro-phenyl]-morpholine (1 g) in THF (20 mL) at 40° C. was added LiAlH4 (500 mg). The reaction mixture was warmed to room temperature and then stirred for 1 hour. The reaction was quenched with water, 10 N sodium hydroxide followed again by water. The resulting mixture was filtered through Celite and the filtrate was concentrated in vacuo. The residue was extracted with CH2Cl2, and the organic layer was washed with water, dried over Na2SO4, filtered and concentrated in vacuo to give 890 mg of the title compound as an oil.

Workup

  1. customThe reaction was quenched with water, 10 N sodium hydroxide
  2. filtrationThe resulting mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. extractionThe residue was extracted with CH2Cl2
  5. washthe organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-163b5dd4977d431fb288f943cfc0ff79
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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