Diethyl Ether → 2,2-Dimethylhexan-1-amine

HRID 26008

Reaction equation

HRID 26008 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:5][CH2:6][CH2:7][CH3:8])[C:3]#[N:4].CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH3:1][C:2]([CH3:9])([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][NH2:4]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 35735622,2-DimethylhexanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 543253312,2-Dimethylhexan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 2,2-dimethylcapronitrile (10.0 g., 0.078 mole) in 100 ml. of ether is added slowly to a suspension of lithium aluminum hydride (6.0 g., 0.158 mole) in 200 ml. of ether while maintaining the reaction at 0°-5°. After stirring the reaction mixture for an additional 2 hr., at 0.5°, the mixture is hydrolyzed by sequentially adding 6.0 ml. of water, 6.0 ml. of 15% sodium hydroxide solution, and finally 18 ml. of water. The hydrolyzed mixture is stirred for an additional hour, filtered and the ether phase concentrated under reduced pressure. Distillation of residual material provides 2,2-dimethylhex-1-ylamine.

Workup

  1. customthe reaction at 0°-5°
  2. customat 0.5°
  3. additionby sequentially adding 6.0 ml
  4. stirringThe hydrolyzed mixture is stirred for an additional hour
  5. filtrationfiltered
  6. concentrationthe ether phase concentrated under reduced pressure
  7. distillationDistillation of residual material

Sources & evidence

ORD record
ord-eeed12b3af744259bd76c2d7e4263f32
Source dataset
uspto-grants-1979_04
Patent number
US04147805

Linked notes

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