HCID 10961905, compound → Tetraethyl aminomethylenediphosphonate

HRID 487050Notes

Reaction equation

HRID 487050 reaction equation
C([N:8]([CH:16]([P:25]([O:30][CH2:31][CH3:32])(=[O:29])[O:26][CH2:27][CH3:28])[P:17]([O:22][CH2:23][CH3:24])(=[O:21])[O:18][CH2:19][CH3:20])CC1C=CC=CC=1)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:8][CH:16]([P:17]([O:22][CH2:23][CH3:24])(=[O:21])[O:18][CH2:19][CH3:20])[P:25]([O:26][CH2:27][CH3:28])(=[O:29])[O:30][CH2:31][CH3:32]

Participants

4

Reactant 1

HCID 10961905HCID 10961905, compound

Product 1

HCID 2773808Tetraethyl aminomethylenediphosphonate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

17.1 g (35.4 mmol) of tetraethyl N,N-dibenzyl-aminomethane-1,1-bisphosphonate are dissolved in 170 ml of ethanol and 3.4 g of 5% strength Pd/C are added. Hydrogenation is carried out at normal pressure. After absorption of 100 ml of hydrogen, a further 3.4 g of 5% strength Pd/C are added and the hydrogenation is completed at normal pressure and room temperature (reaction time about 16 hours). The catalyst is then filtered off with suction. After removal of the solvent, 10.9 g of crude product are obtained. This is purified on a silica gel column using ethanol as the eluent.

Workup

  1. customAfter absorption of 100 ml of hydrogen
  2. additiona further 3.4 g of 5% strength Pd/C are added
  3. customthe hydrogenation is completed at normal pressure and room temperature (reaction time about 16 hours)
  4. filtrationThe catalyst is then filtered off with suction
  5. customAfter removal of the solvent, 10.9 g of crude product
  6. customare obtained
  7. customThis is purified on a silica gel column

Sources & evidence

ORD record
ord-c04f4f2ab1214434962a49c8b3fa8f7a
Source dataset
uspto-grants-1994_03
Patent number
US05294608

Reaction notes

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