Triethylamine → 2-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dione

HRID 970864Notes

Reaction equation

HRID 970864 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].CCN(CC)CC.Br[CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C=O)C>[CH:22]1([CH2:21][O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 140744162-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dioneYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of N-hydroxyphthalimide (10.0 g, 61.30 mmol) in DMF (40 mL) at RT was added NEt3 (9.40 mL, 67.43 mmol) and, in a dropwise fashion, (bromomethyl)cyclohexane (9.41 mL, 67.43 mmol). The reaction was then stirred for 15 hours at 50° C., after which it was allowed to cool to RT and then concentrated under vacuum. The residue was dissolved in Et2O (100 mL) and washed with water, brine, dried over MgSO4 and the solvent removed under reduced pressure. The residue was purified by column chromatography (eluting with CH2Cl2/PE, 1:1 to 3:1) to afford N-(cyclohexylmethoxy)phthalimide (8.40 g, 53%), as a white solid.

Workup

  1. temperatureto cool to RT
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in Et2O (100 mL)
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by column chromatography (eluting with CH2Cl2/PE, 1:1 to 3:1)

Sources & evidence

ORD record
ord-4f03575b0c2a4e62814cb4120aef2577
Source dataset
uspto-grants-2007_12
Patent number
US07312248B2

Reaction notes

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