Phosphoric Acid → HCID 18788097, compound

HRID 1651513Notes

Reaction equation

HRID 1651513 reaction equation
Cl.[CH3:2][C:3]12[CH2:9][C:7]([CH3:10])([CH2:8]1)[CH2:6][N:5]([CH2:11][CH2:12][C:13]([OH:15])=O)[CH2:4]2.[P:16](=[O:20])([OH:19])([OH:18])O.ClC1C=CC=CC=1.P(Cl)(Cl)Cl>O.CO>[CH3:2][C:3]12[CH2:9][C:7]([CH3:10])([CH2:8]1)[CH2:6][N:5]([CH2:11][CH2:12][C:13]([OH:15])([P:16]([OH:20])(=[O:18])[OH:19])[P:16]([OH:19])(=[O:20])[OH:18])[CH2:4]2

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 7964ChlorobenzeneHCID 24387Phosphorus trichlorideHCID 21614498HCID 21614498, compound

Product 1

HCID 18788097HCID 18788097, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

11.68 g (0.05 mol) of 3-(1,5-dimethyl-3-aza-bicyclo[3,1,1]hept-3-yl)-propionic acid hydrochloride, 6.6 ml of 84% phosphoric acid and 23 ml of chlorobenzene are heated to 105° with stirring. 13.5 ml of phosphorus trichloride are slowly added dropwise and the reaction mixture is subsequently maintained at 105° for a further 3 hours. The chlorobenzene is then distilled off under reduced pressure, leaving a viscous mass. 50 ml of water are added to the latter and the mixture is boiled under reflux for 1 hour with stirring. The mixture is then completely concentrated by evaporation under reduced pressure. Upon stirring the residue with acetone and decanting, a colourless oil is obtained which is then dissolved in 50 ml of hot water. Upon adding 140 ml of hot methanol and cooling, colourless crystals of 3-(1,5-dimethyl-3-aza-bicyclo[3,1,1]hept-3-yl)-1-hydroxy-propane-1,1-diphosphonic acid are obtained; m.p. 245°-247° (decomposition); formula ##STR14## The 3-(1,5-dimethyl-3-aza-bicyclo[3,1,1]hept-3-yl)-propionic acid hydrochloride used as starting material can be prepared in the following manner:

Workup

  1. temperaturethe reaction mixture is subsequently maintained at 105° for a further 3 hours
  2. distillationThe chlorobenzene is then distilled off under reduced pressure
  3. customleaving a viscous mass
  4. temperatureunder reflux for 1 hour
  5. stirringwith stirring
  6. concentrationThe mixture is then completely concentrated by evaporation under reduced pressure
  7. stirringUpon stirring the residue with acetone
  8. customdecanting
  9. customa colourless oil is obtained which
  10. temperaturecooling

Sources & evidence

ORD record
ord-d587e8cebadc4d9aa4bc97d477f0b852
Source dataset
uspto-grants-1990_05
Patent number
US04929606

Reaction notes

Loading…