3-(4-Pentylphenyl)propyl mesylate → N-3-(4-pentylphenyl)propylphthalimide
Reaction equation
S(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=1)(=O)(=O)C.[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>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][CH2:6][N:24]2[C:23](=[O:25])[C:22]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]3[C:20]2=[O:30])=[CH:10][CH:11]=1)[CH2:16][CH2:17][CH2:18][CH3:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-(4-pentylphenyl)propyl mesylate (42.4 g, 149 mmol) and potassium phthalimide (27.6 g, 149 mmol) in DMF (200 ml) was stirred at 80° C. for 3 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate anhydride, and the organic layer was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the object compound as an oily substance. 41.1 g, (yield 82%)