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

HRID 1378516Notes

Reaction equation

HRID 1378516 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-ba5e912dbd544896838d27c4550df7c6
Source dataset
uspto-grants-1997_09
Patent number
US05668152

Reaction notes

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