Diisopropylethylamine → 1,1-Dimethylethyl 4-{[5-methyl-4-methoxy-2-nitrophenyl]amino}-1-piperidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

1-Fluoro-5-methyl-4-methoxy-2-nitrobenzene (D17) (0.79 mmol, 146 mg) was treated under argon at room temperature with 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (0.8 mmol, 160 mg, 1 eq) and diisopropylethylamine (0.8 mmol, 103 mg, 1 eq) then stirred at 75° C. overnight. Completion was not observed, and the mixture was heated at higher temperature, 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (0.8 mmol, 160 mg, 1 eq) and diisopropylethylamine (0.8 mmol, 103 mg, 1 eq) were added again and allowed to react overnight at 100° C. The mixture was concentrated under reduced pressure, treated with 10% Na2CO3 aqueous solution and extracted twice with ether. Organics were combined, dried on MgSO4, concentrated under reduced pressure and chromatographed (0-50% ethyl acetate/petrol ether) to give the title compound as an orange residue (0.33 mmol, 120 mg, 42% yield). M+H=310.1, main fragment (molecule has lost its tert-butyl group).

Provenance & Evidence