Water → 2,2,4,4-Tetramethylpentan-3-amine

HRID 1722505Notes

Reaction equation

HRID 1722505 reaction equation
[C:1]([C:5](=[NH:10])[C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH3:2][C:1]([CH3:4])([CH:5]([NH2:10])[C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:3]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 27556322,2,4,4-Tetramethyl-3-pentanone ImineHCID 21226445Aluminium lithium hydride

Product 1

HCID 131658882,2,4,4-Tetramethylpentan-3-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The imine (14 g.) in dry ether (50 ml.) was added to a suspension of lithium aluminum hydride (1.7 g.) in dry ether (50 ml.). The mixture was stirred at room temperature for 24 hours, refluxed two hours and cooled. Water (1.7 ml.), 15% sodium hydroxide solution (5 ml.) and water (5 ml.) were added cautiously in succession, the mixture filtered, concentrated and the residue distilled to afford the desired amine, b.p. 79°-81° C./40 mm.

Workup

  1. temperaturerefluxed two hours
  2. temperaturecooled
  3. filtrationthe mixture filtered
  4. concentrationconcentrated
  5. distillationthe residue distilled

Sources & evidence

ORD record
ord-83cb7febd84e4d948ef9712f9a10fe96
Source dataset
uspto-grants-1989_08
Patent number
US04855454

Reaction notes

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