Acetic Acid → 3-(p-Chlorobenzylamino)propyl(diethoxymethyl)phosphinic acid ethyl ester

HRID 1077691Notes

Reaction equation

HRID 1077691 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH2:10]([O:12][P:13]([CH2:22][CH2:23][CH2:24][NH2:25])([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])=[O:14])[CH3:11].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:10]([O:12][P:13]([CH2:22][CH2:23][CH2:24][NH:25][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])=[O:14])[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10422382Phosphinic acid, (3-aminopropyl)(diethoxymethyl)-, ethyl ester

Product 1

HCID 544329463-(p-Chlorobenzylamino)propyl(diethoxymethyl)phosphinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.41 g of p-chlorobenzaldehyde are added to a solution of 2.53 g of 3-aminopropyl(diethoxymethyl)phosphinic acid ethyl ester in 10 ml of anhydrous methanol, and the resulting clear solution is stirred at room temperature for 30 minutes. There are then added first 0.6 g of glacial acetic acid and then, dropwised, 0.21 g of sodium cyanoborohydride in solution in 5 ml of methanol. An exothermic reaction begins. The mixture is stirred at 20° for 3 hours and adjusted at pH 8, and the solvent is removed. The residue is dissolved in dichlormethane and washed with water. The organic phase is separated off, dried over sodium sulfate and concentrated to dryness by evaporation. The oil that remains is purified by chomatography on silica gel, yielding 3-(p-chlorobenzylamino)propyl(diethoxymethyl)phosphinic acid ethyl ester in the form of a yellowish oil.

Workup

  1. customAn exothermic reaction
  2. stirringThe mixture is stirred at 20° for 3 hours
  3. customthe solvent is removed
  4. dissolutionThe residue is dissolved in dichlormethane
  5. washwashed with water
  6. customThe organic phase is separated off
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to dryness by evaporation
  9. customThe oil that remains is purified by chomatography on silica gel

Sources & evidence

ORD record
ord-ed427b128f5846bd8293872a1fe0b049
Source dataset
uspto-grants-1996_08
Patent number
US05545631

Reaction notes

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