Sodium Carbonate → Butyl phthalimide

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

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):