Methane → 1-Hydroxy-3-(piperidin-2-yl)-propane-1,1-diphosphonic acid

HRID 1073735

Reaktionsgleichung

Reaktionsgleichung von HRID 1073735
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9][C:10]([OH:12])=O.N1C=CC=CC=1CCC(O)=O.[P:24]([OH:27])([OH:26])[OH:25].P(Cl)(Cl)Cl.C.[Na]>Cl.[Pt]=O.O>[OH:12][C:10]([P:24]([OH:27])(=[O:25])[OH:26])([P:24]([OH:27])(=[O:26])[OH:25])[CH2:9][CH2:8][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][NH:2]1

Komponenten

10

Edukt 6

HCID 297MethaneHCID 24387Phosphorus trichlorideHCID 107909Phosphorous acidHCID 5642923-(Pyridin-2-yl)propanoic acidHCID 5360545SodiumHCID 426143813-(Piperidin-2-yl)propanoic acid hydrochloride

Produkt 1

HCID 142312031-Hydroxy-3-(piperidin-2-yl)-propane-1,1-diphosphonic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 82844Platinum oxide (PtO)KatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

1.5 g. 3-(Piperidin-2-yl)-propionic acid hydrochloride (m.p.: 193°-195° C., prepared by hydrogenation of 3-(2-pyridyl)-propionic acid in hydrochloric acid medium in the presence of platinum oxide) and 1.3 g. phosphorous acid are melted together at 80° C. After allowing to cool, 1.4 ml. phosphorus trichloride is added dropwise and further heated for 20 hours to 90° C. After cooling, 20 ml. water are carefully added thereto and heated under reflux for 7 hours. The cooled solution is treated with charcoal, filtered and the filtrate evaporated. After drying, the residue is stirred up several times with acetone, then taken up in water, the solution brought with 2N aqueous sodium hydroxide solution to a pH ≈5 and mixed with methanol. After stirring for some time with ice cooling, the precipitate is filtered off with suction and dried. There is obtained 1.05 g. (37% of theory) of the monosodium salt x 2 mole water; m.p. 270°-274° C.; Mrel : 0.41.

Aufarbeitung

  1. customare melted together at 80° C
  2. temperatureto cool
  3. temperaturefurther heated for 20 hours to 90° C
  4. temperatureAfter cooling
  5. temperatureheated
  6. temperatureunder reflux for 7 hours
  7. filtrationfiltered
  8. customthe filtrate evaporated
  9. customAfter drying
  10. additionmixed with methanol
  11. stirringAfter stirring for some time with ice cooling
  12. filtrationthe precipitate is filtered off with suction
  13. customdried
  14. customThere is obtained 1.05 g

Quellen und Nachweise

ORD-Eintrag
ord-20598a6518244871bb008cfb204bdc1f
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04971958

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