Benzylamine → 1-Benzyl-4-phenyl-1,4-azaphosphinane 4-oxide

HRID 1013499Notes

Reaction equation

HRID 1013499 reaction equation
[C:1]1([P:7](=[O:12])([CH:10]=[CH2:11])[CH:8]=[CH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[CH2:13]([N:20]1[CH2:11][CH2:10][P:7](=[O:12])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7504Benzylamine2×HCID 14223331Diethenylphenylphosphine oxide

Product 1

HCID 579732961-Benzyl-4-phenyl-1,4-azaphosphinane 4-oxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Phenyl(divinyl)phosphine oxide (1.47 g, 8.25 mmol) and benzylamine (901 μL, 8.25 mmol) were combined in water (20 mL) and stirred at 90° C. for 1 h. A second portion of benzylamine (901 mL, 8.25 mmol) was added, and the reaction was stirred at 90° C. for an additional 1 h. The solution was cooled and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated. The crude residue was purified by flash chromatography (0-10% MeOH/CH2Cl2) to afford the desired product as a colorless solid. 1H NMR (CDCl3, 600 MHz) δ 7.79-7.73 (m, 2H), 7.55-7.46 (m, 3H), 7.35-7.30 (m, 4H), 7.27-7.23 (m, 1H), 3.63 (m, 2H), 3.04-2.89 (m, 4H), 2.21-2.14 (m, 2H), 2.08-1.99 (m, 2H). MS: cal'd 286 (MH+), exp 286 (MH+).

Workup

  1. stirringthe reaction was stirred at 90° C. for an additional 1 h
  2. temperatureThe solution was cooled
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude residue was purified by flash chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3eee6e40c067450a8f72ba233d635c10
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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