Ammonia → Ethyl 3-amino-1-methylpropyl(diethoxymethyl)phosphinate

HRID 542294Notes

Reaction equation

HRID 542294 reaction equation
[CH3:1][CH:2]([P:6]([CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])(=[O:10])[O:7][CH2:8][CH3:9])[CH2:3][C:4]#[N:5].N.[H][H]>C(O)C.[Ni]>[NH2:5][CH2:4][CH2:3][CH:2]([P:6]([CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])(=[O:10])[O:7][CH2:8][CH3:9])[CH3:1]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 14362805Ethyl 1-methyl-2-cyanoethyl(diethoxymethyl)phosphinateHCID 178418361HCID 178418361, compound

Product 1

HCID 14362808Ethyl 3-amino-1-methylpropyl(diethoxymethyl)phosphinate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 17.0 g of ethyl 1-methyl-2-cyanoethyl(diethoxymethyl)phosphinate in 150 ml of ethanol is added to 155.0 g of an 8% solution of ammonia in ethanol. To this are added 10 ml of Raney Nickel and the resulting mixture is hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. The mixture is then filtered and the filtrate is concentrated under reduced pressure and the crude product is distilled under reduced pressure to give ethyl 3-amino-1-methylpropyl(diethoxymethyl)phosphinate, b.p. 140° C./0.01 mbar, 31P=+47.0 and +46.7 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-38590387869242bd8ea74cdcf20cd947
Source dataset
uspto-grants-1987_04
Patent number
US04656298

Reaction notes

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