1-Bromo-3-chloropropane → 1-N-[1-N-(3-chloropropyl)-piperidin-4-yl]-indole

HRID 2258576

Reaktionsgleichung

Reaktionsgleichung von HRID 2258576
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][Cl:26]>C(O)C>[Cl:26][CH2:25][CH2:24][CH2:23][N:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 80061-Bromo-3-chloropropane2×HCID 11430Potassium CarbonateHCID 140907551-(Piperidin-4-yl)-1H-indole

Produkt 1

HCID 229072601-N-[1-N-(3-chloropropyl)-piperidin-4-yl]-indoleAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1-(piperidin-4-yl)-indole (100 mg, 0.5 mmol) in absolute ethanol (2 mL) was added anhydrous potassium carbonate (70 mg, 0.5 mmol) and 1-bromo-3-chloropropane (150 mg, 1 mmol). After stirring overnight additional 1-bromo-3-chloropropane (150 mg) was added and stirring continued for 2 hours. The mixture was evaporated; and the residue dissolved in methylene chloride and shaken with water. The organic solution was dried over anhydrous potassium carbonate and evaporated. The residue was chromatographed on silica gel with methylene chloride/ethanol (95:5) to give the title compound (90 mg, 65% yield).

Aufarbeitung

  1. additionwas added
  2. customThe mixture was evaporated
  3. dissolutionand the residue dissolved in methylene chloride
  4. stirringshaken with water
  5. dry with materialThe organic solution was dried over anhydrous potassium carbonate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel with methylene chloride/ethanol (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-e706dfd014a5490990211babd76affc9
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05661173

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