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1,2-Dibromoethane → HCID 18670444, Verbindung

HRID 1059333
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1059333
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Br:32][CH2:33][CH2:34]Br>O1CCCC1.CN(P(N(C)C)(N(C)C)=O)C.CCCCCC.C(OCC)(=O)C.O>[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([CH:26]([CH2:34][CH2:33][Br:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 78391,2-DibromoethaneHCID 7912DiisopropylamineHCID 10400444Ethyl 2-(1-benzylpiperidin-4-yl)acetateHCID 178418339Butyllithium

Produkt 1

HCID 18670444HCID 18670444, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8058HexaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel
HCID 12679HexamethylphosphoramideLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

13 ml of diisopropylamine was dissolved in a solvent mixture of tetrahydrofuran (140 ml) with HMPA (15 ml) in a nitrogen atmosphere and cooled to −78° C. Into the obtained solution was dropped 42 ml of a 2.5 M solution of n-butyllithium in hexane and the resulting mixture was stirred at 0° C. for 30 minutes. After cooling to −78° C. again, 15 ml of a solution of 5.8 g of ethyl (1-benzylpiperidin-4-yl)acetate in tetrahydrofuran was dropped thereinto. The reaction mixture was stirred at 0° C. for 1 hour. Then 1,2-dibromoethane was dropped thereinto at −78° C. again. The reaction mixture was stirred at 0° C. for 30 minutes and then brought back to room temperature. Next, it was distributed into water and ethyl acetate. The organic layer was extracted, washed with water and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 1.40 g of ethyl 2-(1-benzyl-4-piperidyl)-4-bromobutanoate as a colorless oily substance. A solution of 1.40 g of ethyl 2-(1-benzyl-4-piperidyl)-4-bromobutanoate in tetrahydrofuran (20 ml) was stirred at room temperature and 1.0 g of t-butoxypotassium was added thereto. The reaction mixture was distributed into water and ethyl acetate. The organic layer was extracted and washed with water. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 800 mg of the title compound as a colorless oily substance.

Aufarbeitung

  1. temperatureAfter cooling to −78° C. again
  2. stirringThe reaction mixture was stirred at 0° C. for 1 hour
  3. customat −78° C.
  4. stirringThe reaction mixture was stirred at 0° C. for 30 minutes
  5. custombrought back to room temperature
  6. extractionThe organic layer was extracted
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. distillationAfter distilling off the solvent under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-454ab3aed338498cbdfe8dabeb531994
Quelldatensatz
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06518423B1

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