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

HRID 396617Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 396617
[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.Cl[CH2:20][C:21]#[N:22].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][C:21]#[N:22])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 28232394,4-Diphenylpiperidine

Produkt 1

HCID 23004060(4,4-Diphenylpiperidin-1-yl)acetonitrileAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A suspension of 4,4-diphenylpiperidine (4.00 g, 16.9 mmol, 1.00 equiv), chloroacetonitrile (1.40 mL, 21.9 mmol, 1.30 equiv, Aldrich), potassium carbonate (4.67 g, 33.8 mmol, 2.00 equiv), and potassium iodide (561 mg, 3.38 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. The residue was purified by flash chromatography (SiO2, EtOAc) to afford 4.01 g (86%) of white solid, which was characterized spectroscopically.

Aufarbeitung

  1. temperatureat reflux under-argon for 48 hours
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography (SiO2, EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-a4f3de259dc745fa8bcd847bf83bd139
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608086B2

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