Diisopropylethylamine → 1,1-Dimethylethyl 4-({5-methyl-4-[(1-methylethyl)oxy]-2-nitrophenyl}amino)-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 4-fluoro-2-methyl-5-nitrophenyl 1-methylethyl ether (D73) (0.53 mmol, 115 mg) in dimethylformamide (3 mL) was treated with 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (0.53 mmol, 106 mg, 1 eq) and diisopropylethylamine (0.53 mmol, 68.5 mg, 1 eq) under argon at room temperature and then heated at 80° C. overnight. The mixture was then concentrated under reduced pressure, then treated with 10% aqueous sodium carbonate solution and extracted with ether/ethyl acetate. The organics were dried, concentrated under reduced pressure and purified by chromatography on silica (ethyl acetate/petrol ether) to give the title compound as a solid (0.2 mmol, 80 mg, 39% yield). M+H 338.1 for main fragment (loss of tert-butyl group).

Provenance & Evidence