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

HRID 1863870Notes

Reaction equation

HRID 1863870 reaction equation
[CH3:1][P:2](=[O:7])([CH:5]=[CH2:6])[CH:3]=[CH2:4].[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1.O>[CH2:8]([N:15]1[CH2:6][CH2:5][P:2](=[O:7])([CH3:1])[CH2:3][CH2:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 57973285(Ethenyl(methyl)phosphoryl)ethene

Product 1

HCID 668332461-Benzyl-4-methyl-1,4-azaphosphinane 4-oxideYield 64.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of methyl divinyl phosphine oxide (10.73 g, 92.4 mmol) and benzylamine (11.6 mL, 106.3 mmol) in 1:1 THF/water (250 mL) was heated at reflux for 16 hours. The solvents were removed under reduced pressure. The residue was crystallized from CH2Cl2/ether to give 1-benzyl-4-methyl-[1,4]azaphosphinane 4-oxide as a white solid (13.24 g, 64%). 1H NMR (400 MHz, DMSO) δ 7.13-3.37 (5H, m); 3.6 (2H, s); 2.81 (2H, m); 2.59 (2H, m); 1.7-1.9 (4H, m); 1.42 (3H, d, JH-C-P=13.6 Hz). 31P NMR δ32 ppm.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe solvents were removed under reduced pressure
  3. customThe residue was crystallized from CH2Cl2/ether

Sources & evidence

ORD record
ord-640d071d691c462d9ed2aa8b39a5f552
Source dataset
uspto-grants-2009_12
Patent number
US07625880B2

Reaction notes

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