Sodium Iodide → HCID 18993314, compound

HRID 375575Notes

Reaction equation

HRID 375575 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3][CH2:2]1.[CH2:13]1[O:23][C:22]2[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][C:15]=2[O:14]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[CH2:13]1[O:23][C:22]2[CH:21]=[CH:20][C:17]([CH2:18][N:1]3[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3][CH2:2]3)=[CH:16][C:15]=2[O:14]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 2760465Ethyl 2-(piperidin-4-yl)acetate

Product 1

HCID 18993314HCID 18993314, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl piperidine-4-acetate (0.34 g, 2.0 mmol), 3,4-methylenedioxybenzyl chloride (0.34 g, 2.0 mmol), sodium carbonate (1.0 g) and sodium iodide (0.10 g) in acetonitrile (30 ml) was heated under reflux for 16 hours and evaporated. The residue was partitioned between ethyl acetate and water and the organic layer was washed with water, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on SiO2 using dichloromethane plus 0-20% ethyl acetate as eluant. Appropriate fractions were combined and evaporated to give the title compound (0.52 g) as a colourless oil which was characterised by its 1H-NMR spectrum.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and water
  5. washthe organic layer was washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue was purified by chromatography on SiO2
  9. customevaporated

Sources & evidence

ORD record
ord-6e976467bf5846698fd5452e5f5d6b65
Source dataset
uspto-grants-1996_01
Patent number
US05486527

Reaction notes

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