Sodium Carbonate → Butyl phthalimide

HRID 650240Notes

Reaction equation

HRID 650240 reaction equation
COC([C@H]1[C@@H](OC(C2C=CC=CC=2)=O)C[C@H]2N[C@@H]1CC2)=O.Br[CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:37]=[CH:36][CH:35]=[C:29]2[C:30]([NH:32][C:33](=[O:34])[C:28]=12)=[O:31].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[CH2:26]([C:27]1[CH:37]=[CH:36][CH:35]=[C:29]2[C:30]([NH:32][C:33](=[O:34])[C:28]=12)=[O:31])[CH2:25][CH2:24][CH3:23]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 644007(-)-NorcocaineHCID 21960043Bromobutylphthalimide

Product 1

HCID 21190392Butyl phthalimideYield 119.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Norcocaine (268 mg, 0.93 mmol), bromo butylphthalimide (314 mg, 1.11 mmol, 1.2 eq.) and anhydrous sodium carbonate (147 mg, 1.39 mmol, 1.5 eq.) were dissolved in benzene(10 ml) and the mixture was refluxed under nitrogen atmosphere for 72 hours. After cooling to room temperature, the solution was filtered. The filtrate was extracted with 1N hydrochloric acid three times, and the aqueous layer was extracted with chloroform three times. The extract was dried over anhydrous sodium sulfate, and chloroform was distilled off under reduced pressure to give colorless crystal. The crystal was purified by TLC (eluent: ammonia saturated chloform/benzene=1/3) to give a butyl phthalimide derivative (270 mg) of Formula (5):

Workup

  1. temperaturethe mixture was refluxed under nitrogen atmosphere for 72 hours
  2. filtrationthe solution was filtered
  3. extractionThe filtrate was extracted with 1N hydrochloric acid three times
  4. extractionthe aqueous layer was extracted with chloroform three times
  5. dry with materialThe extract was dried over anhydrous sodium sulfate, and chloroform
  6. distillationwas distilled off under reduced pressure
  7. customto give colorless crystal
  8. customThe crystal was purified by TLC (eluent: ammonia saturated chloform/benzene=1/3)

Sources & evidence

ORD record
ord-71f6e6d11507435f9de38cc4e3c90428
Source dataset
uspto-grants-2001_08
Patent number
US06271381B1

Reaction notes

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