Aluminium lithium hydride → 4-[1-(1,1,2,2,2-Pentafluoroethyl)-ethoxy]-benzylamine

HRID 911636Notes

Reaction equation

HRID 911636 reaction equation
[F:1][C:2]([CH:8]([O:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)[CH3:9])([F:7])[C:3]([F:6])([F:5])[F:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[F:1][C:2]([CH:8]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH2:16])=[CH:17][CH:18]=1)[CH3:9])([F:7])[C:3]([F:4])([F:6])[F:5]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 576564594-[1-(1,1,2,2,2-Pentafluoroethyl)-ethoxy]-benzonitrile

Product 1

HCID 576559984-[1-(1,1,2,2,2-Pentafluoroethyl)-ethoxy]-benzylamineYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add (±)-4-[1-(1,1,2,2,2-pentafluoroethyl)-ethoxy]-benzonitrile (1 g, 3.8 mmol) to a slurry of lithium aluminum hydride (400 mg, 10 mmol) in diethyl ether (30 mL) at 0° C. under a nitrogen atmosphere. Stir the mixture at ambient temperature for 2 h, and then quench the reaction sequentially with water (1 mL) and 5N sodium hydroxide (1 mL). Filter the slurry through Celite®, dry the filtrate over Na2SO4, filter and concentrate in vacuo to obtain the title compound (990 mg, 98%). GC-MS m/z: 268 (M+).

Workup

  1. customquench
  2. customthe reaction sequentially with water (1 mL) and 5N sodium hydroxide (1 mL)
  3. filtrationFilter the slurry through Celite®
  4. dry with materialdry the filtrate over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-4e9c0f96353f4c55a013a5e47b865152
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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