1,1-Cyclohexanedicarbonitrile → [1-(Aminomethyl)cyclohexyl]methanamine

HRID 1024343

Reaction equation

HRID 1024343 reaction equation
[C:1]1([C:9]#[N:10])([C:7]#[N:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[NH2:8][CH2:7][C:1]1([CH2:9][NH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 5445611,1-CyclohexanedicarbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 71994[1-(Aminomethyl)cyclohexyl]methanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Cyclohexane-1,1-dicarbonitrile (20.0 g) was taken up in dry Et2O (70 mL). This mixture was added dropwise to a suspension of LiAlH4 (17.0 g) in dry Et2O (250 mL) cooled in an ice bath. The mixture was stirred overnight at room temperature, cooled in an ice bath, and quenched by adding H2O (17.0 mL), 2M aqueous NaOH (34.0 mL) and again H2O (17 mL). The suspension was filtered, the filter cake was washed with Et2O, and the combined filtrates were evaporated to dryness yielding 20.8 g of a clear, colorless liquid. 1H NMR (400 MHz, CDCl3) δ 1.05-1.55 (m, 14H), 2.61 (s, 4H).

Workup

  1. temperaturecooled in an ice bath
  2. temperaturecooled in an ice bath
  3. customquenched
  4. additionby adding H2O (17.0 mL), 2M aqueous NaOH (34.0 mL) and again H2O (17 mL)
  5. filtrationThe suspension was filtered
  6. washthe filter cake was washed with Et2O
  7. customthe combined filtrates were evaporated to dryness
  8. customyielding 20.8 g of a clear, colorless liquid

Sources & evidence

ORD record
ord-29bcc19f59174ca69225c1ba4463760d
Source dataset
uspto-grants-2014_05
Patent number
US08722887B2

Linked notes

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