3-Aminopropyl(phenyl)phosphinic acid → 3-Aminopropyl(cyclohexyl)phosphinic acid

HRID 2050696Notes

Reaction equation

HRID 2050696 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])[OH:6].[H][H]>O.Cl>[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)(=[O:6])[OH:7]

Participants

5

Reactant 2

HCID 101042063-Aminopropyl(phenyl)phosphinic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 99207013-Aminopropyl(cyclohexyl)phosphinic acidYield 5,311.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 1.5 g of 3-aminopropyl(phenyl)phosphinic acid in 10 ml of water and 7.9 ml of 1N hydrochloric acid is treated with hydrogen at 25° in the presence of 0.2 g of Nishimura-catalyst (Rh/PtO2). After 1.2 hours hydrogen up-take stops. The reaction mixture is filtered and the filtrate evaporated to dryness. The residue is recrystallized from methanol/propylenoxide to give 1.2 g of 3-aminopropyl(cyclohexyl)phosphinic acid x 0,4 mol hydrochloric acid as a white solid, m.p. 202-203°.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate evaporated to dryness
  3. customThe residue is recrystallized from methanol/propylenoxide

Sources & evidence

ORD record
ord-ae2f5ae6bc124127b1c71c06525ba10d
Source dataset
uspto-grants-1991_05
Patent number
US05013863

Reaction notes

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