Diethyl Ether → Diphenyl 1-(n-allyl)amino-4-pyridylmethyl-phosphonate

HRID 1935661Notes

Reaction equation

HRID 1935661 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].C(=O)([O-])[O-].[Na+].[Na+].[C:11]1([O:17][P:18]([O-:26])[O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])C.[CH3:34][CH2:35]OCC>>[CH2:1]([NH:4][N:29]1[CH:30]=[CH:31][C:34]([CH2:35][P:18](=[O:26])([O:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:33][CH2:32]1)[CH:2]=[CH2:3]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 7853AllylamineHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 23418553Diphenoxyphosphanolate

Product 1

HCID 22463870Diphenyl 1-(n-allyl)amino-4-pyridylmethyl-phosphonate

Procedure

To a solution of 4-pyridinecarboxyaldehyde (1.01 g,10 mmol) and allylamine (0.61 g,10 mmol) in ether (30 ml) was added anhydrous sodium carbonate (2.76 g). The solution was stirred at r.t. overnight, then sodium carbonate was filtered off. To the reaction mixture, diphenylphosphite (2.34 g,10 mmol) and triethylamine (1.01 g,10 mmol) were added with cooling over an ice-water bath. It was stirred at r.t. overnight. After removal of the solvent an oily residue was obtained which was chromatographed (1:1 Petroleum ether/ethyl acetate) to give 2.85 g (65%) as an oil.

Workup

  1. filtrationsodium carbonate was filtered off
  2. temperaturewith cooling over an ice-water bath
  3. stirringIt was stirred at r.t. overnight
  4. customAfter removal of the solvent an oily residue
  5. customwas obtained which
  6. customwas chromatographed (1:1 Petroleum ether/ethyl acetate)
  7. customto give 2.85 g (65%) as an oil

Sources & evidence

ORD record
ord-398e056465de4b4eaad1bc22555eeb26
Source dataset
uspto-grants-2002_05
Patent number
US06387881B1

Reaction notes

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