Potassium Carbonate → HCID 90014067, compound

HRID 1499014Notes

Reaction equation

HRID 1499014 reaction equation
O[CH2:2][CH2:3][NH:4][CH2:5][CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10].[C:15]([O-])([O-])=O.[K+].[K+].ClCCC[C:25]#[N:26]>C(#N)C>[C:25]([CH:2]([CH3:15])[CH2:3][NH:4][CH2:5][CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])#[N:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123364-ChlorobutyronitrileHCID 54204764HCID 54204764, compound

Product 1

HCID 90014067HCID 90014067, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-10 °C

Procedure

The mixture of diethyl 2-(2-hydroxyethylamino)ethylphosphonate (6 g, 26.7 mmol) and K2CO3 (3.7 g, 26.7 mmol) in dry acetonitrile (80 ml) was cooled to −10° C. and 4-chlorobutyronitrile (4.16 g, 40 mmol) was added. The reaction mixture was stirred at −10° C. for 1 h and then heated at 80° C. for 70 h. The solvent was then removed by evaporatation. Water and CHCl3 were added, the organic layer separated, washed with brine and dried over anhydrous MgSO4. After filtration, solvent was evaporated and the residue was purified by column chromatography on silica gel (CHCl3-MeOH), the diethyl 2-(2-cyanopropylamino)ethylphosphonate was obtained in 69% yield (5.38 g).

Workup

  1. temperatureheated at 80° C. for 70 h
  2. customThe solvent was then removed by evaporatation
  3. additionWater and CHCl3 were added
  4. customthe organic layer separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationAfter filtration, solvent
  8. customwas evaporated
  9. customthe residue was purified by column chromatography on silica gel (CHCl3-MeOH)

Sources & evidence

ORD record
ord-e9f47743305847eab5c4a663c4c31244
Source dataset
uspto-grants-2015_12
Patent number
US09200020B2

Reaction notes

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