Methanol → N-(2-methoxyethyl)-N-methyl-4-nitrobenzylamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromomethyl-4-nitro-benzene (86.4 mg, 0.4 mmol) in tetrahydrofuran (800 μL) is added triethylamine (200 μL) and 2-(methoxyethyl)methylamine (43 μL, 0.4 mmol). The reaction mixture is shaken at 50° C. for 5 hours. To the reaction mixture is then added 500 μL each of tetrahydrofuran and methanol followed by 350 mg of PS-Ph3P resin to remove unreacted alkyl bromide and shaken for 1 h. The resin is filtered off, rinsed with dichloromethane and the filtrate concentrated. To the residue is added 500 μL each of tetrahydrofuran and methanol followed by 350 mg of PS-TsOH resin to remove unreacted amine. This is then shaken for two hours, filtered, washed with dichloromethane, and concentrated to yield (2-methoxy-ethyl)-methyl-(4-nitro-benzyl)-amine, which is used as such for the subsequent reaction.

Provenance & Evidence