1,1-Dicyanocyclopentane → 1,1-Cyclopentanedimethanamine

HRID 1024340

Reaction equation

HRID 1024340 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:14]#[N:15])([C:12]#[N:13])[CH2:11][CH2:10][CH2:9][CH2:8]1>CCOCC>[NH2:13][CH2:12][C:7]1([CH2:14][NH2:15])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 151720351,1-DicyanocyclopentaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 4325931,1-Cyclopentanedimethanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of LiAlH4 (4.74 g) in dry Et2O (100 mL) was cooled in an ice bath, and a solution of cyclopentane-1,1-dicarbonitrile (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 4.95 g of a clear, colorless liquid. 1H NMR (400 MHz, CDCl3) δ 1.24 (br s, 4H), 1.22-1.40 (m, 4H), 1.55-1.64 (m, 4H), 2.62 (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 4.95 g of a clear, colorless liquid

Sources & evidence

ORD record
ord-2847da0268104ceb836d3f501da542f8
Source dataset
uspto-grants-2014_05
Patent number
US08722887B2

Linked notes

Loading…