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Hydrochloric Acid → HCID 57127353, Verbindung

HRID 1955063
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1955063
[CH3:1][C:2]([C:4]1[CH:15]=[CH:14][C:7]2[N:8]([CH2:12][CH3:13])[C:9]([CH3:11])=[N:10][C:6]=2[CH:5]=1)=[O:3].[CH:16]([CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19]1)=O.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl>O1CCCC1.O>[CH2:12]([N:8]1[C:7]2[CH:14]=[CH:15][C:4]([C:2](=[O:3])[CH:1]=[CH:16][CH:18]3[CH2:19][CH2:20][N:21]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:22][CH2:23]3)=[CH:5][C:6]=2[N:10]=[C:9]1[CH3:11])[CH3:13]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 895841-Benzylpiperidine-4-carbaldehydeHCID 2733832Lithium hexamethyldisilazaneHCID 51735161-(1-ethyl-2-methylbenzimidazol-5-yl)ethanone

Produkt 1

HCID 57127353HCID 57127353, VerbindungAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A mixture of 0.1 g (0.5 mM) of 1-ethyl-2-methylbenzimidazole-5-yl methyl ketone and 0.1 g (0.5 mM) 4-formyl-N-benzylpiperidine in 10 mL of tetrahydrofuran (THF) was cooled to -78° C. under a nitrogen atmosphere. To this mixture were added dropwise 0.5 mL (0.5 mM) of a IM solution of lithium bis(trimethylsilyl)amide in THF. The reaction was stirred at -78° C. for 1 hour, then warmed to room temperature. To the reaction was added 10 mL of water and the pH was adjusted to 2.0 with 1N hydrochloric acid (HCl). The mixture was extracted with 15 mL of ethyl acetate. The pH of the water layer was then sequentially adjusted to 3.0, 4.0, 5.0, 6.5, and 8.5 with IN NaOH, each time extracting with 15 mL of ethyl acetate. The ethyl acetate extracts at pH=5.0 and 6.5 were combined, dried with sodium sulfate (Na2SO4) and evaporated to yield 50 mg (26%) of the title compound as an oil.

Aufarbeitung

  1. temperaturewarmed to room temperature
  2. extractionThe mixture was extracted with 15 mL of ethyl acetate
  3. extractioneach time extracting with 15 mL of ethyl acetate
  4. dry with materialdried with sodium sulfate (Na2SO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9993d18ec7c24106b70ced67464d9a43
Quelldatensatz
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06124321

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