Potassium Iodide → 2-[2-(Benzodioxan-6-yl)ethylamino]-1-(diphenylmethoxy)-2-methylpropane

HRID 1613171Notes

Reaction equation

HRID 1613171 reaction equation
[NH2:1][C:2]([CH3:19])([CH3:18])[CH2:3][O:4][CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[CH2:21][CH2:22][C:23]1[CH:32]=[CH:31][C:26]2[O:27][CH2:28][CH2:29][O:30][C:25]=2[CH:24]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[O:27]1[C:26]2[CH:31]=[CH:32][C:23]([CH2:22][CH2:21][NH:1][C:2]([CH3:19])([CH3:18])[CH2:3][O:4][CH:5]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:24][C:25]=2[O:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 190885086-(2-Bromoethyl)-2,3-dihydro-1,4-benzodioxinHCID 197753022-Amino-1-diphenylmethoxy-2-methylpropane

Product 1

HCID 678852442-[2-(Benzodioxan-6-yl)ethylamino]-1-(diphenylmethoxy)-2-methylpropane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-amino-1-diphenylmethoxy-2-methylpropane (369 mg -- see Preparation 1), 6-(2-bromoethyl)benzodioxan (243 mg -- see Preparation 10), potassium carbonate (415 mg) and potassium iodide (166 mg) in acetonitrile (40 ml) was heated under reflux for 48 hours and evaporated. The residue was partitioned between ethyl acetate and water and the organic layer was washed with water, dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica (7 g) using ethyl acetate plus 0-5% methanol as the eluant. Appropriate fractions were combined and evaporated to give the title compound as a colourless oil which was characterised as a hemihydrate (130 mg, 31%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 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 sodium sulphate
  7. customevaporated
  8. customThe residue was purified by chromatography on silica (7 g)
  9. customevaporated

Sources & evidence

ORD record
ord-4051eba82e3549c5a6ea136cb7244fbd
Source dataset
uspto-grants-1993_03
Patent number
US05192765

Reaction notes

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