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

HRID 921414Notes

Reaction equation

HRID 921414 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 70.3%

Reagents, catalysts & solvents 1

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

Procedure

A solution of methyl divinyl phosphine oxide (1.16 g, 10.0 mmol) and benzylamine (1.20 mL, 11.0 mmol) in 1:1 THF/water (25 mL) was heated at reflux for 16 h. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane) to afford 1-benzyl-4-methyl-[1,4]azaphosphinane-4-oxide as a white solid (1.57 g, 70% yield).

Workup

  1. temperatureat reflux for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane)

Sources & evidence

ORD record
ord-139d0d9ddcea4e31963458b0f2a6cc9c
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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