Potassium Cyanide → HCID 54536415, Verbindung

HRID 1870249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1870249
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]

Komponenten

5

Edukt 3

HCID 9032Potassium Cyanide2×HCID 2855718-Crown-6HCID 57124706HCID 57124706, Verbindung

Produkt 1

HCID 54536415HCID 54536415, VerbindungAusbeute 37,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e4a85dd66ac14169a9192db57be028ca
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06096736

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