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

HRID 44133

반응식

HRID 44133 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5e9d866dabef4d8192a6503e58e2576a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541343B2

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