Potassium Cyanide → HCID 54536415、化合物

HRID 1870251ノート

反応式

HRID 1870251 の反応式
Br[CH2:2][C@@H:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1.[C-:24]#[N:25].[K+]>CS(C)=O>[C:24]([CH2:2][C@@H:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4]1)#[N:25]

参加物

4

反応物 2

HCID 9032Potassium CyanideHCID 56975661HCID 56975661、化合物

生成物 1

HCID 54536415HCID 54536415、化合物収率 83.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
47.5 °C

実験手順

A mixture of (5S)-5-bromomethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.83 g), potassium cyanide (0.27 g) and dimethyl sulfoxide (9 ml) is heated with stirring at 45-50° C. for three hours. To the reaction solution is added ice, and the mixture is extracted with ethyl acetate--diethyl ether. The extract is dried over sodium sulfate, and evaporated under reduced pressure to remove the solvent. The resulting residue is purified by silica gel column chromatography (solvent; n-hexane: ethyl acetate=6:1), and recrystallized from ethyl acetate--n-hexane to give (5R)-5-cyanomethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.60 g).

後処理

  1. temperatureis heated
  2. additionTo the reaction solution is added ice
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialThe extract is dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe resulting residue is purified by silica gel column chromatography (solvent; n-hexane: ethyl acetate=6:1)
  8. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-69087f85f68240c68246d7cd6c46d502
出典データセット
uspto-grants-2000_08
特許番号
US06096736

反応ノート

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