2,2-Diethylmalononitrile → 1,3-Diamino-2,2-diethylpropane

HRID 1024337Notes

Reaction equation

HRID 1024337 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:9]([CH2:14][CH3:15])([C:12]#[N:13])[C:10]#[N:11])[CH3:8]>CCOCC>[CH2:7]([C:9]([CH2:14][CH3:15])([CH2:12][NH2:13])[CH2:10][NH2:11])[CH3:8]

Participants

4

Reactant 2

HCID 27772312,2-DiethylmalononitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 4325891,3-Diamino-2,2-diethylpropane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of LiAlH4 (4.66 g) in dry Et2O (100 mL) was cooled in an ice bath, and a solution of 2,2-diethyl-malononitrile (5.0 g) in Et2O (50 mL) was added dropwise at such a rate that the temperature was kept below 20° C. The mixture was stirred overnight at room temperature, cooled in an ice bath, and quenched by adding H2O (5 mL), 2M aqueous NaOH (10 mL) and again H2O (5 mL). The suspension was filtered, the filter cake was washed with Et2O, and the combined filtrates were evaporated to dryness under reduced pressure to give 5.0 g of a clear, light-yellow liquid. 1H NMR (400 MHz, CDCl3) δ 0.80 (t, J=8 Hz, 6H), 1.08 (br s, 4H), 1.22 (q, J=8 Hz, 4H), 2.52 (s, 4H).

Workup

  1. temperaturewas cooled in an ice bath
  2. customwas kept below 20° C
  3. temperaturecooled in an ice bath
  4. customquenched
  5. additionby adding H2O (5 mL), 2M aqueous NaOH (10 mL) and again H2O (5 mL)
  6. filtrationThe suspension was filtered
  7. washthe filter cake was washed with Et2O
  8. customthe combined filtrates were evaporated to dryness under reduced pressure
  9. customto give 5.0 g of a clear, light-yellow liquid

Sources & evidence

ORD record
ord-2b4ed2c08f70401892cf94dae688719d
Source dataset
uspto-grants-2014_05
Patent number
US08722887B2

Reaction notes

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