Ammonia → Isopropyl 3-aminopropyl(ethyl)phosphinate

HRID 973600Notes

Reaction equation

HRID 973600 reaction equation
[C:1]([CH2:3][CH2:4][P:5]([CH2:11][CH3:12])(=[O:10])[O:6][CH:7]([CH3:9])[CH3:8])#[N:2].N.[H][H]>C(O)(C)C.[Ni]>[NH2:2][CH2:1][CH2:3][CH2:4][P:5]([CH2:11][CH3:12])(=[O:10])[O:6][CH:7]([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 19090919Isopropyl 2-cyanoethyl(ethyl)phosphinateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 19090904Isopropyl 3-aminopropyl(ethyl)phosphinate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

To 34.1 g of isopropyl 2-cyanoethyl(ethyl)phosphinate in 500 ml of isopropanol are added 60 ml of liquid ammonia and 6.8 g of Raney-Nickel. The mixture is heated to 80° and treated with hydrogen at 100 bar. After 11/2 hours hydrogen-uptake stops. The reaction mixture is filtered and the filtrate distilled to give isopropyl 3-aminopropyl(ethyl)phosphinate as a colorless oil, b.p. 75°/13 Pa.

Workup

  1. temperatureThe mixture is heated to 80°
  2. filtrationThe reaction mixture is filtered
  3. distillationthe filtrate distilled

Sources & evidence

ORD record
ord-ff16bdb929314dc681e94f113da0277a
Source dataset
uspto-grants-1991_11
Patent number
US05064819

Reaction notes

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