HCID 19028856, compound → HCID 19029000, compound

HRID 2256342Notes

Reaction equation

HRID 2256342 reaction equation
I[CH2:2][CH2:3][C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][O:6][CH2:5]1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[K]>CN(C=O)C>[C:14]1([C:4]2([CH2:3][CH2:2][N:24]3[C:23](=[O:25])[C:22]4=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]4[C:20]3=[O:30])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][O:6][CH2:5]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 19028856HCID 19028856, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 19029000HCID 19029000, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of synthesized 4-(2-iodoethyl)-4-phenylisochroman (0.5 g) and potassium phthalimide (0.51 g) was heated in DMF (10 ml) at 60° C. with stirring for 14 hours. The reaction mixture was then poured in ice-water and the syrup separating out was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified by silica gel column chromatography and recrystallized from ethyl acetate-hexane to provide the title compound (0.12 g) as colorless needless.

Workup

  1. customthe syrup separating out
  2. extractionwas extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by silica gel column chromatography
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e843ad319a984cc58ba2452bb6b9fb24
Source dataset
uspto-grants-1997_08
Patent number
US05654296

Reaction notes

Loading…