Trimethylsilyl cyanide → 1-Dimethylamino-4-(N',N'-dimethyl-hydrazino)-piperidine-4-carbonitrile

HRID 44133

Reaktionsgleichung

Reaktionsgleichung von HRID 44133
[CH3:1][N:2]([CH3:13])[N:3]=[C:4]1[CH2:9][CH2:8][N:7]([N:10]([CH3:12])[CH3:11])[CH2:6][CH2:5]1.C[Si]([C:18]#[N:19])(C)C>O>[CH3:11][N:10]([CH3:12])[N:7]1[CH2:8][CH2:9][C:4]([NH:3][N:2]([CH3:13])[CH3:1])([C:18]#[N:19])[CH2:5][CH2:6]1

Komponenten

4

Edukt 2

HCID 82115Trimethylsilyl cyanideHCID 67227495[4-(Dimethyl-hydrazono)-piperidin-1-yl]-dimethyl-amine

Produkt 1

HCID 672283611-Dimethylamino-4-(N',N'-dimethyl-hydrazino)-piperidine-4-carbonitrileAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2.25 g [4-(Dimethyl-hydrazono)-piperidin-1-yl]-dimethyl-amine (from Step 1) is dissolved in 25 ml water, cooled in an ice bath, and 3.64 g trimethylsilyl cyanide is added at such a rate, that the internal temperature does not exceed 10° C. Then the mixture is stirred at ambient temperature for 18 hours, extracted with ethyl acetate, the organic layer washed with brine, dried over sodium sulfate, and the solvent evaporated, to give 2.1 g 1-Dimethylamino-4-(N′,N′-dimethyl-hydrazino)-piperidine-4-carbonitrile. 1H-NMR (CDCl3): 2.74 ppm (m, 2H), 2.50 ppm (m, 2H), 2.40 ppm (s, 6H), 2.35 ppm (s, broad, 1H), 2.24 ppm (s, 6H), 1.95 ppm (m, 2H), 1.60 ppm (m, 2H).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customdoes not exceed 10° C
  3. extractionextracted with ethyl acetate
  4. washthe organic layer washed with brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-5e9d866dabef4d8192a6503e58e2576a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541343B2

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