Hydrochloric Acid → HCID 12753802, compound

HRID 1657990Notes

Reaction equation

HRID 1657990 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.[ClH:18]>C(O)C.[Pd]>[ClH:18].[NH2:8][CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10923173Diethyl (benzylamino)methylphosphonate

Product 1

HCID 12753802HCID 12753802, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent3×

Procedure

A solution of diethyl N-benzylaminomethylphosphonate (30.1 g., 0.117 mole) in absolute ethanol (400 ml.) is treated with 0.9 N HCl in ethanol (130 ml.) and hydrogenated at 45 psi with 10% palladium on carbon (6.6 g.) for 19 hours. The resulting mixture is filtered through a packed pad of diatomaceous earth to remove the catalyst. Evaporation of the filtrate under reduced pressure gives a clear residue which is successively dissolved in ethanol and benzene and evaporated in vacuo to give diethyl aminomethylphosphonate hydrochloride (23.2 g.) as a white powder. nmr (DMSO-d6)τ 8.73 (t, 6, J=7Hz, CH2CH3), 6.76 (d, 2, J=13.5Hz, CH2), 5.87 (d of q, 4, J=7Hz and J=8Hz, CH2) and 1.42 (br s, 3, NH3).

Workup

  1. filtrationThe resulting mixture is filtered through a packed pad of diatomaceous earth
  2. customto remove the catalyst
  3. customEvaporation of the filtrate under reduced pressure
  4. customgives a clear residue which
  5. custombenzene and evaporated in vacuo

Sources & evidence

ORD record
ord-552431e3837a426f8c80f94ecc06ad59
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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