N-Benzylphthalimide

white crystalline powder

N-Benzylphthalimide may be used in the following syntheses:

• 2-benzyl-1,1,3,3-tetraphenylisoindoline
• tailor-made highly fluorous porphyrin derivatives
• N-benzylisoindole

ChEBI: N-Benzylphthalimide is a member of isoindoles.

In a flask equipped with a reflux condenser, a mixture of 300 gm (2.04 mole) of phthalimide, 140 gm (1.09 mole) of potassium carbonate, and 300 gm (2.37 mole) of benzyl chloride is refluxed for 3 hr. The excess benzyl chloride is removed by steam distillation and the benzyl phthalimide which crystallizes out is filtered by suction. The product is washed with water, with 400 ml of 60% ethanol, and then dried to afford 360-375 gm (74-77%), m.p. 116°C (recrystallized from acetic acid).

Organic Syntheses, Coll. Vol. 2, p. 83, 1943
The Journal of Organic Chemistry, 47, p. 2785, 1982 DOI: 10.1021/jo00135a021
Tetrahedron Letters, 11, p. 2691, 1970

N-Benzylphthalimide (NBPT), also known as 2-benzylisoindoline-1,3-dione, is an N-substituted phthalimide. It has been prepared by reacting phthalic anhydride with benzyl amine in glacial acetic acid. Vibrational spectra of NBPT has been recorded and assigned. NBPT is a roof-shaped molecule with a planar cyclic imide and a phenyl ring connected by a methylene group. Crystal structure of N-benzylphthalimide has parallel layers of phthalimides stack along the a axis.