Diethyl (cyanomethyl)phosphonate → Diethyl (2-aminoethyl)phosphonate

HRID 424301Notes

Reaction equation

HRID 424301 reaction equation
[C:1]([CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])#[N:2]>C(O)C.Cl.[Pd]>[NH2:2][CH2:1][CH2:3][P:4](=[O:11])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10]

Participants

5

Reactant 1

HCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 2733596Diethyl (2-aminoethyl)phosphonateYield 63%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of diethyl cyanomethylphosphonate (17.7 g; 0.1 moles) in ethanol (70 ml) and aqueous HCl (40 ml of 10% HCl) over 10% Pd/C (1 g) is stirred in a pressure vessel at 60 psi. When the calculated amount of H2 had been absorbed (about 26 hours), the catalyst is filtered off over Celite, washed with ethanol, and the filtrate is neutralized with NaHCO3 and evaporated to dryness under vacuum. The residue is extracted with absolute ethanol (2×50 ml) and the clear extract is distilled at about 110° C. and 0.18 mbar to give a colorless liquid (11.4 g; yield 63%).

Workup

  1. customWhen the calculated amount of H2 had been absorbed (about 26 hours)
  2. filtrationthe catalyst is filtered off over Celite
  3. washwashed with ethanol
  4. customevaporated to dryness under vacuum
  5. extractionThe residue is extracted with absolute ethanol (2×50 ml)
  6. extractionthe clear extract
  7. distillationis distilled at about 110° C.
  8. custom0.18 mbar to give a colorless liquid (11.4 g; yield 63%)

Sources & evidence

ORD record
ord-c7e25341d01c4823a0c7313dcf290e21
Source dataset
uspto-grants-2012_01
Patent number
US08105689B2

Reaction notes

Loading…