Benzyl Bromide → HCID 66571516, compound

Participants

Reaction Conditions

Reaction Steps

N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (50 mg, 0.133 mmol) was dissolved in 0.5 mL of DMF and cooled to 0° C. Lithium bis(trimethylsilyl)amide (0.146 ml, 0.146 mmol) was added dropwise and the reaction was allowed to stir for 10 minutes. (bromomethyl)benzene (0.024 ml, 0.200 mmol) was added to the reaction, and was allowed to stir overnight at room temperature. The reaction showed disappearance of the majority of the starting material. The reaction was quenched with water. It was then extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution three times and dried over magnesium sulfate, filtered and concentrated. The crude material was purified through silica gel chromatography using 25% EtOAc:DCM. 1H-NMR (400 MHz, DMSO -d6) 7.64-7.55, 7.42-7.15, 7.13-7.06, 6.75-6.68, 5.56-5.47, 4.64, 4.57-3.91, 3.21-2.89, 2.78, 1.92-1.20

Provenance & Evidence