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Potassium Iodide → 4-(4,4-Diphenylpiperidin-1-yl)butyronitrile

HRID 964224
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 964224
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:20][CH2:21][CH2:22][C:23]#[N:24].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC.O1CCOCC1>[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8][CH2:9][N:10]([CH2:20][CH2:21][CH2:22][C:23]#[N:24])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 28232394,4-Diphenylpiperidine

Produkt 1

HCID 230041164-(4,4-Diphenylpiperidin-1-yl)butyronitrileAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 263
1-Butanol
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A suspension of 4,4-diphenylpiperidine (4.15 g, 17.5 mmol, 1.00 equiv), 4-bromobutyronitrile (2.10 mL, 21.0 mmol, 1.20 equiv, Aldrich), potassium carbonate (4.85 g, 35.0 mmol, 2.00 equiv), and potassium iodide (581 mg, 3.50 mmol, 0.20 equiv) in n-butanol (20 mL) and 1,4-dioxane (20 mL) was stirred at reflux under argon for 48 hours. The mixture was cooled to room temperature and concentrated. Water (50 mL) was added and the mixture was extracted with CH2Cl2 (4×150 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, EtOAc) to afford 4.65 g (87%) of white solid, which was characterized spectroscopically.

Aufarbeitung

  1. temperatureat reflux under argon for 48 hours
  2. concentrationconcentrated
  3. additionWater (50 mL) was added
  4. extractionthe mixture was extracted with CH2Cl2 (4×150 mL)
  5. dry with materialThe combined organic solutions were dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (SiO2, EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-2ffb45e656774db78a79afc14a2a968a
Quelldatensatz
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05767131

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