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Acetic Acid → 4-[4-(Diethoxyphosphorylmethylsulfonyl)piperazin-1-yl]-2-methyl-quinoline

HRID 333933
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 333933
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:32]([O:34][P:35](Cl)([O:37][CH2:38][CH3:39])=[O:36])[CH3:33].C(O)(=O)C>C1COCC1.O>[CH2:32]([O:34][P:35]([CH2:21][S:18]([N:15]1[CH2:14][CH2:13][N:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([CH3:1])[CH:11]=2)[CH2:17][CH2:16]1)(=[O:20])=[O:19])([O:37][CH2:38][CH3:39])=[O:36])[CH3:33]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 13139Diethyl chlorophosphateHCID 2733832Lithium hexamethyldisilazaneHCID 668358192-Methyl-4-(4-methylsulfonylpiperazin-1-yl)quinoline

Produkt 1

HCID 866915914-[4-(Diethoxyphosphorylmethylsulfonyl)piperazin-1-yl]-2-methyl-quinolineAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-Methyl-4-(4-methylsulfonylpiperazin-1-yl)quinoline (70 mg, 0.23 mmol) was placed in a Schlenk tube under an argon atmosphere, anhydrous THF (1.5 ml) was added and the solution cooled to −78° C. Lithium hexamethyldisilazid (50.6 mmol, 50.6 μl of a 1M solution in anhydrous THF) was added dropwise and the mixture stirred for one hour at −78° C. Diethylchlorophosphate (33.3 μl, 0.23 mmol) was added dropwise and stirring was continued for one hour. Acetic acid (100 μl) and water (1.5 ml) were added, the temperature raised slowly to room temperature and the mixture was extracted with diethylether (3×). The combined organic phases were washed with water and brine and evaporated to dryness under reduced pressure. 99 mg of an oily residue were obtained (0.22 mmol, 98%). MS (APCI) m/z=441.7 [M+1]+.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for one hour
  3. temperaturethe temperature raised slowly to room temperature
  4. extractionthe mixture was extracted with diethylether (3×)
  5. washThe combined organic phases were washed with water and brine
  6. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aabd939b1fc54fb99154219a2c342035
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08883791B2

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