Diethyl (benzylamino)methylphosphonate → Diethyl (aminomethyl)phosphonate

HRID 870136Notes

Reaction equation

HRID 870136 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-ee3306a6d62b48dc884c95f95a73112f
Source dataset
uspto-grants-2015_03
Patent number
US08969377B2

Reaction notes

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