Propylene Oxide → (3-Aminopropyl)(n-butyl)phosphinic acid

HRID 973592Notes

Reaction equation

HRID 973592 reaction equation
C(O[N:9](C12C(C)(C)C1CCC(C)C2=O)[CH2:10][CH2:11][CH2:12][P:13]([CH2:16][CH2:17][CH2:18][CH3:19])(=[O:15])[OH:14])C1C=CC=CC=1.C1OC1C>Cl.CO>[NH2:9][CH2:10][CH2:11][CH2:12][P:13]([CH2:16][CH2:17][CH2:18][CH3:19])(=[O:14])[OH:15]

Participants

5

Reactant 2

HCID 6378Propylene OxideHCID 867451993-(Benzyloxycaronylamino)propyl(n-butyl)phosphinic acid

Product 1

HCID 130021(3-Aminopropyl)(n-butyl)phosphinic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 6.7 g of 3-(benzyloxycaronylamino)propyl(n-butyl)phosphinic acid in 125 ml of 36% hydrochloric acid is heated at reflux for 1.5 hour. The mixture is evaporated to an oil and the oil is co-evaporated with water (2×50 ml) to give a white solid. This solid is then dissolved in 50 ml of dry methanol, 1-3 ml of propylene oxide is added and the solution is stirred at room temperature. The precipitated product is collected by filtration and dried to give 3-aminopropyl(n-butyl)phosphinic acid, m.p. 231°-234° (dec.), 31P-NMR : δ=+44.6 ppm (D2O).

Workup

  1. temperatureat reflux for 1.5 hour
  2. customThe mixture is evaporated to an oil
  3. customto give a white solid
  4. filtrationThe precipitated product is collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-6ae35effed4044a08e3f88fdebf8de8f
Source dataset
uspto-grants-1991_11
Patent number
US05064819

Reaction notes

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