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

HRID 1612882

反応式

HRID 1612882 の反応式
[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

参加物

5

反応物 3

HCID 5925Dibenamine hydrochlorideHCID 8794PhenylacetonitrileHCID 2733832Lithium Hexamethyldisilazide

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c8eeb9d2ead14d3bbc0fb1dc636b3199
出典データセット
uspto-grants-1993_03
特許番号
US05190922

関連ノート

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