Hydrazine hydrate (1:1) → Diethyl (3-aminopropyl)phosphonate

HRID 2044134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2044134
O.NN.C1(=O)[N:8]([CH2:9][CH2:10][CH2:11][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])C(=O)C2=CC=CC=C12>C(O)C>[NH2:8][CH2:9][CH2:10][CH2:11][P:12](=[O:19])([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 2542412-(3-Diethoxyphosphorylpropyl)isoindole-1,3-dione

Produkt 1

HCID 78113Diethyl (3-aminopropyl)phosphonateAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To this end, 23.08 g (46.1 mmol) of hydrazine monohydrate are added dropwise to 15 g (46.1 mmol) of diethyl phthalimidopropylphosphonate in about 500 ml of absolute ethanol. The reaction medium is stirred for 12 hours. The salts formed are filtered off and washed with ethanol. After evaporating off the ethanol, salts are again formed. These salts are washed with CH2Cl2 and filtered on a Millipore membrane (0.45 μm). The filtrate is recovered and the CH2Cl2 is evaporated off. A yellow oil is obtained. The crude product is purified by chromatography on a column of silica gel with a 90/10 CHCl3/MeOH mixture as eluent. 4.6 g of diethyl 3-aminopropylphosphonate (APPE) are obtained in a yield of 51.8%.

Aufarbeitung

  1. customThe salts formed
  2. filtrationare filtered off
  3. washwashed with ethanol
  4. customAfter evaporating off the ethanol, salts
  5. customare again formed
  6. washThese salts are washed with CH2Cl2
  7. filtrationfiltered on a Millipore membrane (0.45 μm)
  8. customThe filtrate is recovered
  9. customthe CH2Cl2 is evaporated off
  10. customA yellow oil is obtained
  11. customThe crude product is purified by chromatography on a column of silica gel with a 90/10 CHCl3/MeOH mixture as eluent

Quellen und Nachweise

ORD-Eintrag
ord-d1cc997cbfaf4af4805305dfe34eb75d
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586758B2

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