Sodium Iodide → HCID 9931689, compound

HRID 2225430Notes

Reaction equation

HRID 2225430 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[CH2:27][CH2:28]Br.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C.C(OCC)(=O)C.O>[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([CH2:28][CH2:27][C:26]3[CH:30]=[CH:31][CH:32]=[C:24]([O:23][CH3:22])[CH:25]=3)[CH2:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 1374501-Bromo-2-(3-methoxyphenyl)ethaneHCID 190042093-[(Diphenylmethoxy)methyl]piperidine

Product 1

HCID 9931689HCID 9931689, compoundYield 53.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(diphenylmethoxymethyl)piperidine (1.40 g, 5.0 mmol--see Preparation 1), 3-methoxyphenethyl bromide (1.08 g, 5.0 mmol), sodium carbonate (1.08 g) and sodium iodide (0.10 g) in acetonitrile (30 ml) was heated under reflux for 18 hours, diluted with ethyl acetate and water and the layers separated. The organic layer was washed with water, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-3% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (1.12 g) as a colourless oil which was characterised containing a third of an equivalent of water.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customthe layers separated
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by chromatography on silica
  8. customevaporated

Sources & evidence

ORD record
ord-d302f6fa7bfc4ad2a3bc81a6629f4545
Source dataset
uspto-grants-1994_09
Patent number
US05344835

Reaction notes

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