Phthalimide potassium salt → HCID 7663500, compound

HRID 1618388Notes

Reaction equation

HRID 1618388 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)(=O)=O.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CN(C=O)C>[Br:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][CH2:7][CH2:6][N:20]1[C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]2[C:16]1=[O:26]

Participants

4

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 57608391HCID 57608391, compound

Product 1

HCID 7663500HCID 7663500, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of mesylate 16 (24.05 g, 81.5 mmol) in anhydrous DMF (160 ml) was added potassium phthalimide (15.53 g, 83.8 mmol) and the reaction mixture stirred at 60° C. for 14 h. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was diluted with hexanes-EtOAc (7:1, 150 ml) and water (150 ml) and the mixture shaken in separating funnel. A precipitate formed which was removed by filtration, washed excessively with water and hexane, then dried under vacuum to give N-(2-(3-bromophenoxy)ethyl)phthalimide (17) as white fluffy crystals (22.05 g, 78%). The organic layer of the filtrate was concentrated under reduced pressure and the residue was suspended in 10% EtOAc-hexanes. The solution was washed with water and the precipitate collected by filtration, washed with water then hexanes and dried under vacuum to give additional phthalimide 17 (5.65 g). Combined yield (21.18 g, 98%): 1H NMR (400 MHz, CDCl3) δ 7.86 (m, 2H), 7.73 (m, 2H), 7.03-7.12 (m, 3H), 6.80 (ddd, J=8.0, 2.5 and 1.4 Hz, 1H), 4.21 (t, J=6.9 Hz, 2H), 4.10 (t, J=6.0 Hz, 2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with hexanes-EtOAc (7:1, 150 ml) and water (150 ml)
  4. stirringthe mixture shaken
  5. customin separating funnel
  6. customA precipitate formed which
  7. customwas removed by filtration
  8. washwashed excessively with water and hexane
  9. customdried under vacuum

Sources & evidence

ORD record
ord-663cba3b42854991af781e3b79606bb8
Source dataset
uspto-grants-2014_07
Patent number
US08766007B2

Reaction notes

Loading…