Ammonia → isobutyl P-(3-aminopropyl)-P-methyl-phosphinate

HRID 2210762Notes

Reaction equation

HRID 2210762 reaction equation
[C:1]([CH2:3][CH2:4][P:5]([CH3:12])(=[O:11])[O:6][CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2].N.[H][H]>C(O)C.[Ni]>[NH2:2][CH2:1][CH2:3][CH2:4][P:5]([CH3:12])(=[O:11])[O:6][CH2:7][CH:8]([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 2304642isobutyl P-(2-cyanoethyl)-P-methyl-phosphinateHCID 178418361HCID 178418361, compound

Product 1

HCID 23374769isobutyl P-(3-aminopropyl)-P-methyl-phosphinate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 20.0 g of isobutyl P-(2-cyanoethyl)-P-methyl-phosphinate in 200 ml of ethanol is added to 230.0 g of an 8% solution of ammonia in ethanol. To this are added 15 ml of Raney nickel slurry and the resulting mixture is hydrogenated at 1 bar until hydrogen uptake ceases. The mixture is then filtered and the filtrate is concentrated under reduced pressure. The crude product is distilled under reduced pressure to give isobutyl P-(3-aminopropyl)-P-methyl-phosphinate, b.p. 130°/0.01 mbar, 31P-NMR spectrum: δ=+57.6 ppm (CDCl3).

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. distillationThe crude product is distilled under reduced pressure

Sources & evidence

ORD record
ord-346ce8e3169a493f89fa986580fa4503
Source dataset
uspto-grants-1995_10
Patent number
US05461040

Reaction notes

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