Potassium Iodide → 8-(3-(piperidin-1-yl)propoxy)-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one

HRID 506642Notes

Reaction equation

HRID 506642 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]2[N:11]3[CH2:15][CH2:16][NH:17][C:18](=[O:19])[C:10]3=[CH:9][C:8]=2[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C(=O)(O)[O-].[Na+]>CC(=O)CC>[N:28]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:12]3[N:11]4[CH2:15][CH2:16][NH:17][C:18](=[O:19])[C:10]4=[CH:9][C:8]=3[CH:7]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 684653958-(3-chloro-propoxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Product 1

HCID 166795198-(3-(piperidin-1-yl)propoxy)-3,4-dihydropyrazino[1,2-a]indol-1(2H)-oneYield 39%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The suspension consistent of 0.27 g (0.97 mmol) 8-(3-chloro-propoxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one, 0.16 g (1.2 mmol) potassium carbonate, 0.16 g (0.97 mmol) potassium iodide and 0.12 ml (99 μg, 1.2 mmol) piperidine (commercially available) in 10 mL 2-butanone was heated under reflux for 19 hours. After cooling down to room temperature the reaction mixture was poured on saturated aqueous sodium bicarbonate solution water and was extracted three times with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed on silica gel with dichloromethane: methanol:ammonia (9:1:0.1 v/v) as eluant to give 0.12 g (39%) of the desired compound as a colorless solid.

Workup

  1. temperatureunder reflux for 19 hours
  2. extractionwas extracted three times with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was flash-chromatographed on silica gel with dichloromethane: methanol:ammonia (9:1:0.1 v/v) as eluant

Sources & evidence

ORD record
ord-1880fa64c316462e99c723cac3c4ea4b
Source dataset
uspto-grants-2010_08
Patent number
US07786109B2

Reaction notes

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