Ammonia → Ethyl 3-amino-l-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate

HRID 5174Notes

Reaction equation

HRID 5174 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([P:12]([CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])(=[O:16])[O:13][CH2:14][CH3:15])[CH2:9][C:10]#[N:11])=[CH:4][CH:3]=1.N.[H][H]>C(O)C.[Ni]>[NH2:11][CH2:10][CH2:9][CH:8]([P:12]([CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])(=[O:16])[O:13][CH2:14][CH3:15])[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 14362807Ethyl 1-(4-chlorophenyl)-2-cyanoethyl(diethoxymethyl)phosphinateHCID 178418361HCID 178418361, compound

Product 1

HCID 14362810Ethyl 3-amino-l-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 20 g of ethyl 1-(4-chlorophenyl)-2-cyanoethyl(diethoxymethyl)phosphinate in 85 ml of ethanol is added to 131 g of an 8% solution of ammonia in ethanol. To this are added 8.5 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, the filtrate is concentrated under reduced pressure and the crude product is distilled under reduced pressure to give ethyl 3-amino-1-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate, b.p. 190° C./0.02 mbar, 31P=+41.5 and +41.3 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-ccb1ee78f6554d898be6494680e71a61
Source dataset
uspto-grants-1993_09
Patent number
US05243062

Reaction notes

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