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

HRID 44133

Reaction equation

HRID 44133 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 672283611-Dimethylamino-4-(N',N'-dimethyl-hydrazino)-piperidine-4-carbonitrileYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5e9d866dabef4d8192a6503e58e2576a
Source dataset
uspto-grants-2013_09
Patent number
US08541343B2

Linked notes

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