Azobisisobutyronitrile → Butyl ethyl(3-aminopropyl)phosphinate

HRID 1912021Notes

Reaction equation

HRID 1912021 reaction equation
[CH2:1]([P:3]([O-:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2].[CH2:10]([NH2:13])[CH:11]=[CH2:12].CC(N=NC(C#N)(C)C)(C#N)C>C(O)CCC>[CH2:1]([P:3]([CH2:12][CH2:11][CH2:10][NH2:13])(=[O:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 7853AllylamineHCID 86614949Butyl ethyiphosphonite

Product 1

HCID 46212699Butyl ethyl(3-aminopropyl)phosphinateYield 65.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

150 g (1 mol) of butyl ethylphosphonite (produced as in Example 2) and 68.4 g (1.2 mol) of allylamine are initially charged in 200 ml of butanol in a four-neck round-bottom flask equipped with stirrer, reflux condenser, thermometer and nitrogen inlet, and heated. At about 100° C., in the course of 1 h, 98.4 g of a 5% solution of AIBN in butanol are added dropwise, whereafter the solvent is distilled off in vacuo. Chromatographic purification yields 135 g (65% of theory) of butyl ethyl(3-aminopropyl)phosphinate.

Workup

  1. customequipped with stirrer
  2. temperaturereflux condenser
  3. temperaturethermometer and nitrogen inlet, and heated
  4. distillationis distilled off in vacuo
  5. customChromatographic purification

Sources & evidence

ORD record
ord-648ac24811eb4fe29028af2f65dc5e13
Source dataset
uspto-grants-2013_12
Patent number
US08604232B2

Reaction notes

Loading…