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

HRID 382677
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 382677
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

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 mol, 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-6ae90e1658564f289159f67fcd904ad0
Quelldatensatz
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06310076B1

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