Potassium Cyanide → HCID 54536415, 화합물

HRID 1870249노트

반응식

HRID 1870249 반응식
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]

참가 물질

5

반응물 3

HCID 9032Potassium Cyanide2회HCID 2855718-Crown-6HCID 57124706HCID 57124706, 화합물

생성물 1

HCID 54536415HCID 54536415, 화합물수율 37.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e4a85dd66ac14169a9192db57be028ca
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06096736

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