Sodium Iodide → HCID 23175711, compound

HRID 2225436Notes

Reaction equation

HRID 2225436 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:8][CH2:9][CH:10]2[CH2:14][CH2:13][NH:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]1[O:32][C:31]2[CH:30]=[CH:29][C:25]([CH2:26][CH2:27]Br)=[CH:24][C:23]=2[O:22]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C.O.C(OCC)(=O)C>[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:8][CH2:9][CH:10]2[CH2:14][CH2:13][N:12]([CH2:27][CH2:26][C:25]3[CH:29]=[CH:30][C:31]4[O:32][CH2:21][O:22][C:23]=4[CH:24]=3)[CH2:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 122072243,4-Methylenedioxyphenethyl bromideHCID 19004210HCID 19004210, compound

Product 1

HCID 23175711HCID 23175711, compoundYield 52.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(diphenylmethoxymethyl)pyrrolidine (267 mg) (Preparation 7), 3,4-methylenedioxyphenethyl bromide (250 mg), sodium carbonate (1.0 g) and sodium iodide (100 mg) in acetonitrile (30 ml) was heated under reflux for 24 hours, diluted with water and ethyl acetate and the layers separated. The organic layer was washed with water, dried over magnesium sulphate and evaporated. The residue was purified by chromatogrpahy on silica using dichloromethane plus 0-20% ethyl acetate followed by dichloromethane plus 20% ethyl acetate plus 1-5% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (217 mg) as a colourless oil which was characterised containing 0.25 equivalents of water.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 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 chromatogrpahy on silica
  8. customevaporated

Sources & evidence

ORD record
ord-a61073ac67d64a36982e471f21be54a9
Source dataset
uspto-grants-1994_09
Patent number
US05344835

Reaction notes

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