Potassium Cyanide → HCID 54536415、化合物

HRID 1870249ノート

反応式

HRID 1870249 の反応式
I[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+].C1OCCOCCOCCOCCOCCOC1>CN(C)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

5

反応物 3

HCID 9032Potassium Cyanide2 回HCID 2855718-Crown-6HCID 57124706HCID 57124706、化合物

生成物 1

HCID 54536415HCID 54536415、化合物収率 37.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

A mixture of (5S)-5-iodomethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (1.41 g), potassium cyanide (0.42 g), a catalytic amount of 18-crown-6 and dimethylformamide (16 ml) is heated with stirring at 85° C. for one hour. To the mixture is added potassium cyanide (0.42 g), and the mixture is further stirred at 85° C. for totally 6 hours. To the reaction solution is added ice, and the mixture is extracted with ethyl acetate--toluene. The extract is dried over sodium sulfate, and concentrated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=4:1), and recrystallized from ethyl acetate--n-hexane to give (5R)-5-cyanomethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.41 g).

後処理

  1. stirringthe mixture is further stirred at 85° C. for totally 6 hours
  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. concentrationconcentrated under reduced pressure
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=4:1)
  8. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-e4a85dd66ac14169a9192db57be028ca
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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