Synthetic Route of 17564-64-6,Some common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, molecular formula is C9H6ClNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
tert-Butyl 3-bromo-4-oxo-piperidine-1-carboxylate (2 g, 7.2 mmol) was suspended in THF (2 mL) and cooled in an ice bath before addition of dimethylamine (16 mL of 2 M, 32 mmol). Upon complete addition, the ice bath was removed and the mixture was stirred at ambient temperature for 16 hours. The mixture was partitioned between saturated aqueous sodium bicarbonate solution and EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was dissolved in THF (28 mL) under N2. The solution was cooled to -78 C and LiHMDS (10 mL of 1 M, 10 mmol) was added dropwise. After 40 minutes, 2- (chloromethyl)isoindoline-1,3-dione (2.32 g, 11.8 mmol) was added in portions over 5 minutes. The solution was stirred for 1 hour then left to warm up to 0 C before being quenched by addition of saturated aqueous NH4Cl solution. The mixture was partitioned between saturated aqueous sodium bicarbonate solution and EtOAc. The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica, 0-10% MeOH/DCM gradient elution) to give tert-butyl 3-(dimethylamino)-5-[(1,3-dioxoisoindolin-2- yl)methyl]-4-oxo-piperidine-1-carboxylate (1.58 g, 50%); MS m/z: 402 (M+H)+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Chloromethyl)isoindoline-1,3-dione, its application will become more common.