Reacción #1951052

ord-640d071d691c462d9ed2aa8b39a5f552

Ecuación de reacción

C=CP(C)(=O)C=C
methyl divinyl phosphine oxide
NCc1ccccc1
benzylamine
CP1(=O)CCN(Cc2ccccc2)CC1
1-benzyl-4-methyl-[1,4]azaphosphinane 4-oxide
Rendimiento 64.2%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07625880B2uspto-grants-2009_12