Potassium Cyanide → 3-Methyl-2-(methylamino)-3-phenylbutanenitrile

HRID 966431

Reaktionsgleichung

Reaktionsgleichung von HRID 966431
[C-:1]#[N:2].[K+].Cl.[CH3:5][NH2:6].[CH3:7][C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH:9]=O>O.CO>[CH3:7][C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH:9]([NH:6][CH3:5])[C:1]#[N:2]

Komponenten

6

Edukt 3

HCID 9032Potassium CyanideHCID 2838792-Methyl-2-phenylpropanalHCID 6364545Methylamine hydrochloride

Produkt 1

HCID 117081933-Methyl-2-(methylamino)-3-phenylbutanenitrileAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

To a solution of potassium cyanide (103 g, 1.56 mol) and methylamine hydrochloride (106 g, 1.56 mol) in water (1000 mL) is added a solution of 2-methyl-2-phenylpropanal (222 g, 1.50 mol) in methanol (1000 mL) over a period of 30 minutes. An ice-water bath is used occasionally to maintain the reaction temperature between 20-25° C. The mixture is stirred at room temperature for 25 hours. Water (2000 mL) is then added and the reaction mixture is extracted with CH2Cl2 (3×800 mL). The combined organic extracts are washed with brine (500 mL) and dried over Na2SO4. The organic extracts are filtered and concentrated to give 3-methyl-2-(methylamino)-3-phenylbutanenitrile as an oil (274 g, 95% yield, 76.6% by HPLC area, NMR (>95%)). Evidence of decomposition on the HPLC/GC column is noted.

Aufarbeitung

  1. customAn ice-water bath is used occasionally
  2. extractionthe reaction mixture is extracted with CH2Cl2 (3×800 mL)
  3. washThe combined organic extracts are washed with brine (500 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe organic extracts are filtered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-229183f5043d4bfca086d132b31a2fc5
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951955B2

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