Dibenamine hydrochloride → alpha-(N,N-dibenzylaminoethyl) benzyl cyanide

HRID 1612882

반응식

HRID 1612882 반응식
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl.Cl[CH2:22][CH2:23][N:24]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[CH2:32]([N:24]([CH2:23][CH2:22][CH:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

참가 물질

5

반응물 3

HCID 5925Dibenamine hydrochlorideHCID 8794PhenylacetonitrileHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 54062416alpha-(N,N-dibenzylaminoethyl) benzyl cyanide수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

Benzyl cyanide (0.97 mL, 8.4 mmole) was reacted with lithium bis(trimethylsilyl)amide (LHMDSA) (8.4 mL, 8.4 mmole) in 5 mL of THF at -78° C. for 1 hour. After an additional aliquot of LHMDSA (4.2 mL, 4.2 mmole) was added, N-(2-chloroethyl)dibenzylamine hydrochloride (1.0 g, 3.4 mmole) was then added. The reaction was allowed to stand at room temperature and was then warmed to 50° C. for 3.5 hours. The mixture was poured into ice/water, and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford alpha-(N,N-dibenzylaminoethyl) benzyl cyanide (1.05 g), isolated in 94% yield (MS: (M+H)+ =341).

후처리

  1. additionAfter an additional aliquot of LHMDSA (4.2 mL, 4.2 mmole) was added
  2. customto stand at room temperature
  3. extractionthe product was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c8eeb9d2ead14d3bbc0fb1dc636b3199
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05190922

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