Water → 2,2-Dihexylpropane-1,3-diamine

HRID 329586Notes

Reaction equation

HRID 329586 reaction equation
[CH2:1]([C:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([C:10]#[N:11])[C:8]#[N:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[H][H]>C(OCC)C>[CH2:12]([C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])([CH2:8][NH2:9])[CH2:10][NH2:11])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 19755212DihexylpropanedinitrileHCID 21226445Aluminium lithium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 197552132,2-Dihexylpropane-1,3-diamineYield 49.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2,2-Dihexylpropanedinitrile (22.0 g, 94 mmol) dissolved in dry diethyl ether (100 ml) was added slowly to a suspension of lithium aluminium hydride (8.7 g, 0.23 mol) in dry diethyl ether (250 ml) under nitrogen. Upon complete addition, the mixture was heated under reflux using a water bath for 1 h and then stirred at room temperature for 24 h. Water was carefully added to the reaction mixture with cooling of the flask in an ice bath, until no more hydrogen was evolved. The reaction mixture separated into two layers and the ether layer was decanted from the aqueous layer, washed with water, and dried with anhydrous magnesium sulphate. The ether was evaporated to yield a viscous oil that was distilled under reduced pressure to yield 2,2-dihexylpropane-1,3-diamine as a colorless liquid (11.2 g, 49%) b.p. 138°-142° C./0.7 mm.

Workup

  1. additionUpon complete addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux
  4. customfor 1 h
  5. customThe reaction mixture separated into two layers
  6. customthe ether layer was decanted from the aqueous layer
  7. washwashed with water
  8. dry with materialdried with anhydrous magnesium sulphate
  9. customThe ether was evaporated
  10. customto yield a viscous oil that
  11. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-03cce46fc7024cb0ac46df81e96b54e3
Source dataset
uspto-grants-1990_01
Patent number
US04892806

Reaction notes

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