Diethyl (benzylamino)methylphosphonate → Diethyl (aminomethyl)phosphonate

HRID 1470082Notes

Reaction equation

HRID 1470082 reaction equation
C([NH:8][CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])C1C=CC=CC=1>C(O)C.C(O)(=O)C.[C].[Pd]>[NH2:8][CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]

Participants

5

Reactant 1

HCID 10923173Diethyl (benzylamino)methylphosphonate

Product 1

HCID 1596920Diethyl (aminomethyl)phosphonate

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A 250-mL pressure tank reactor was purged, flushed and maintained with a hydrogen atmosphere, then, was added a solution of diethyl (benzylamino)methylphosphonate (3.5 g, 13.62 mmol, 1.00 equiv) in ethanol (180 mL), acetic acid (10 mL) and Palladium carbon (0.2 g, 0.10 equiv). The resulting solution was stirred for 24 h at 50° C. under 20 atm pressure. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 2.0 g (crude) of the title compound as brown oil which was used without further purification.

Workup

  1. customA 250-mL pressure tank reactor was purged
  2. customflushed
  3. temperaturemaintained with a hydrogen atmosphere
  4. filtrationThe solids were filtered out
  5. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-951beb50351f424b9e56eae91691c4ae
Source dataset
uspto-grants-2015_04
Patent number
US09006281B2

Reaction notes

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