Potassium Carbonate → [3-(4-Indol-1-yl-piperidin-1-yl)-propyl]-dimethylamine

HRID 2258577Notes

Reaction equation

HRID 2258577 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)[CH2:7][CH2:6]1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:27][NH2+:28][CH3:29]>C(O)C>[N:11]1([CH:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH2:2][N:28]([CH3:29])[CH3:27])[CH2:6][CH2:7]2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18348643Dimethylammonium hydrochlorideHCID 229072601-N-[1-N-(3-chloropropyl)-piperidin-4-yl]-indole

Product 1

HCID 22907270[3-(4-Indol-1-yl-piperidin-1-yl)-propyl]-dimethylamineYield 107.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-N-[1-N-(3-chloro-propyl)-piperidin-4-yl]-indole (900 mg, 3.25 mmol), anhydrous potassium carbonate (440 mg, 3.25 mmol) and dimethylammonium hydrochloride (260 mg, 3.25 mmol) in absolute ethanol (10 mL) was refluxed for 6 hours, evaporated and suspended in water. The mixture was extracted with methylene chloride, dried over anhydrous potassium carbonate, and evaporated to yield 1 g of the desired compound (100% of theory).

Workup

  1. temperaturewas refluxed for 6 hours
  2. customevaporated
  3. extractionThe mixture was extracted with methylene chloride
  4. dry with materialdried over anhydrous potassium carbonate
  5. customevaporated

Sources & evidence

ORD record
ord-501b026e01ee401895d0880519f2f065
Source dataset
uspto-grants-1997_08
Patent number
US05661173

Reaction notes

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