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

HRID 1077931Notes

Reaction equation

HRID 1077931 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a7cdccc42e614c7e8f078cb53fa5b16f
Source dataset
uspto-grants-1996_08
Patent number
US05545636

Reaction notes

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