2142-01-0

Usage

Uses

Used in Chemical Syntheses:
N-Benzylphthalimide is used as a key intermediate in the synthesis of various organic compounds, including 2-benzyl-1,1,3,3-tetraphenylisoindoline and tailor-made highly fluorous porphyrin derivatives. It serves as a crucial building block for the development of complex molecular structures with potential applications in various fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-Benzylphthalimide is utilized as a starting material for the synthesis of various pharmaceutical compounds, such as N-benzylisoindole. These synthesized compounds can be further used in the development of drugs with specific therapeutic properties.
Used in Research and Development:
N-Benzylphthalimide is also employed in research and development for the study of its chemical properties, reactivity, and potential applications in the synthesis of novel compounds. The vibrational spectra of NBPT have been recorded and assigned, providing valuable information for researchers working with N-BENZYLPHTHALIMIDE.

Preparation

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).

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 83, 1943The Journal of Organic Chemistry, 47, p. 2785, 1982 DOI: 10.1021/jo00135a021Tetrahedron Letters, 11, p. 2691, 1970

InChI:InChI=1/C15H11NO2/c17-14-12-8-4-5-9-13(12)15(18)16(14)10-11-6-2-1-3-7-11/h1-9H,10H2

Upstream product

• 136918-14-4 phthalimide 
• 100-44-7 benzyl chloride 
• 1074-82-4 potassium phtalimide 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 100-46-9 benzylamine 
• 33704-38-0 2-(benzylsulfinothioyl)isoindoline-1,3-dione 
• 100-39-0 benzyl bromide 
• 123-72-8 butyraldehyde 
• 100422-85-3 (α-phthalimidobenzyl)trimethylsilane 
• 52826-45-6 (benzylimino)triphenylphosphorane 
• 88-95-9 Phthaloyl dichloride 
• 4333-67-9 (E)-3-(2'-oxo-2'-phenyl)ethylidene isobenzofuran-1(3H)-one 
• 524-38-9 N-hydroxyphthalimide 
• 1914-20-1 N-methoxyphthalimide 

Downstream Products

• 136918-14-4 phthalimide 
• 100965-07-9 N-(α-bromo-benzyl)-phthalimide 
• 100-52-7 benzaldehyde 
• 135382-78-4 ZIN⁽⁰¹⁶⁾C₀₀₆₅₁ 
• 82894-83-5 2-benzyl-1,1,3,3-tetramethylisoindoline 
• 86166-00-9 2-benzyl-1-ethyl-1,3,3-trimethylisoindoline 
• 35180-14-4 N-benzylisoindoline 
• 25473-60-3 2-benzyl-2H-isoindole 
• 35970-03-7 2-(2-nitrobenzyl)isoindoline-1,3-dione 
• 62133-07-7 2-(4-nitrobenzyl)-1H-isoindole-1,3(2H)-dione 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 100-46-9 benzylamine 
• 219908-57-3 2-hydroxy-1,3-dimethyl-1,3-diphenylisoindoline 
• 3792-71-0 2-benzyl-1,1,3,3-tetraethylisoindoline 

Relevant academic research and scientific papers

Comparative study of chemically immobilized and conventional homogeneous ionic liquids as phase-transfer catalysts for the N -alkylation of heterocyclic compounds

Various ionic liquids (ILs) were screened for their phase-transfer catalytic (PTC) activity using the N-alkylation of nitrogen heterocycles as the model reaction. Immobilized ILs behaved extremely well and proved to be far better catalysts than conventional homogeneous PTCs in terms of their stability, easy recovery, and reusability. The investigation also demonstrated that quaternary tetraalkylammonium salts offer very high catalytic activity, whereas aromatic heterocyclic tetravalent nitrogen catalysts (imidazolium- and pyridinium-based salts) were poorly active.

Efficient one-pot synthesis of N-substituted phthalimides/naphthalimides from azides and anhydrides by iodotrimethylsilane

N-Substituted phthalimides and naphthalimides have been obtained in good to excellent yields, employing chlorotrimethylsilane and sodium iodide (in situ generation of iodotrimethylsilane) from corresponding azides and anhydrides under mild conditions.

A Facile One-pot Synthesis of N-Substituted Phthalimides Using a Catalytic Amount of Crown Ether

N-Substituted phthalimides, intermediates of the Gabriel synthesis, were obtained in high yields (84-100percent) by the addition of a catalytic amount of 18-crown-6 to the reaction of potassium phthalimide and alkyl halides in toluene.

Wavelength dependent photoextrusion and tandem photo-extrusion reactions of ninhydrin bis-acetals for the synthesis of 8-ring lactones, benzocyclobutenes and orthoanhydrides

Ninhydrin bis-acetals give access to 8-ring lactones, benzocyclo-butenes and spirocyclic orthoanhydrides through photoextrusion and tandem photoextrusion reactions. Syntheses of fimbricalyxlactone B, isoshihunine and numerous biologically-relevant heteroc

An Oxidation Study of Phthalimide-Derived Hydroxylactams

A systematic study of the oxidation of 3-hydroxy-2-substituted isoindolin-1-ones (hy-droxylactams) and their conversion to the corresponding phthalimides was undertaken using three oxidants. Of special interest was the introduction of nickel peroxide (NiO2 ) as an oxidation system for hydroxylactams and comparison of its performance with the commonly used pyridinium chlorochromate (PCC) and iodoxybenzoic acid (IBX) reagents. Using a range of hydroxylactams, optimal conversions of these substrates to the corresponding imides was achieved with 50 equivalents of freshly prepared NiO2 in refluxing toluene over 5–32 h reaction times. By comparison, oxidations of the same substrates using PCC/silica gel (three equivalents) and IBX (three equivalents) required oxidation times of 1–3 h for full conversion but required lengthier purification. While nominal amounts (~25 mg) of substrate hydroxylactams were used to ascertain conversion, scale-up procedures using all three methods gave good to excellent isolated yields of imides.

Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams

An efficient and practical electrochemical method for selective reduction of cyclic imides has been developed using a simple undivided cell with carbon electrodes at room temperature. The reaction provides a useful strategy for the rapid synthesis of hydroxylactams and lactams in a controllable manner, which is tuned by electric current and reaction time, and exhibits broad substrate scope and high functional group tolerance even to reduction-sensitive moieties. Initial mechanistic studies suggest that the approach heavily relies on the utilization of amines (e.g., i-Pr2NH), which are able to generate α-aminoalkyl radicals. This protocol provides an efficient route for the cleavage of C-O bonds under mild conditions with high chemoselectivity.

Tunable System for Electrochemical Reduction of Ketones and Phthalimides

Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously choosing the solvent and an acidic additive. The reaction conditions were compatible with a diverse array of functional groups, and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds. Mechanistic studies showed that the reactions involved electron, proton, and hydrogen atom transfers. Importantly, an N3/HN3 cycle operated as a hydrogen atom shuttle, which was critical for reduction of the carbonyl groups to methylene groups.

Visible-Light-Induced Controlled Oxidation of N-Substituted 1,2,3,4-Tetrahydroisoquinolines for the Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones and Isoquinolin-1(2H)-ones

A visible light-rose bengal-TBHP mediated, controlled oxidation of N-substituted 1,2,3,4-tetrahydroisoquinolines is developed for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and isoquinolin-1(2H)-ones. The present method feature's a broad substrate scope, good functional group tolerances, and the products were prepared in good to excellent yields. The developed methodology further demonstrated in the synthesis of isoindolo[2,1-b] isoquinolin-5(7H)-one (topoisomerase-I inhibitor). (Figure presented.).

“On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides

An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.

One-Pot Substitution of Aliphatic Alcohols Mediated by Sulfuryl Fluoride

The Mitsunobu reaction is a powerful transformation for the one-pot activation and substitution of aliphatic alcohols. Significant efforts have focused on modifying the classic conditions to overcome problems associated with purification from phosphine-based byproducts. Herein, we report a phosphine free method for alcohol activation and substitution that is mediated by sulfuryl fluoride. This new method is effective for a wide range of primary alcohols using phthalimide, di-tert-butyl-iminodicarboxylate, and aromatic thiol nucleophiles in 74 % average yield. Activated carbon nucleophiles and a deactivated phenol were also effective for this reaction in good yields. Secondary alcohols were also successful substrates using aryl thiols, affording the corresponding sulfides in 56 % average yield with enantiomeric ratios up to 99:1. This new protocol has a distinct synthetic advantage over many existing phosphine-based methods as the byproducts are readily separable. This feature was exploited in several examples that did not require chromatography for purification. Furthermore, the mild reaction conditions enabled further in situ derivatization for the one-pot conversion of alcohols to amines or sulfones. This method also provides a boarder nucleophile scope compared to existing phosphine-free methods.