tert-butyl N-(4-aminobutyl)carbamate → HCID 86684852, compound

Participants

Reaction Steps

To a stirred solution of N-Boc-1,4-butanediamine (0.400 g; 2.12 mmol) and 1-fluoro-2,4-dinitrobenzene (280 μL; 2.23 mmol) in anhydrous tetrahydrofuran (THF) (10 mL) was added triethylamine (886 μL; 6.36 mmol). The reaction solution was stirred at ambient temperature for 17 hours and was then concentrated. The residue was dissolved in ethyl acetate and washed with water, saturated NaHCO3 and saturated NaCl. The organic solution was dried over MgSO4 and concentrated to give a yellow oil (1.12 g). Purification using a Thomson Instruments Single StEP™ silica gel column (25 g) and eluting with 20% ethylacetate/80% hexanes followed by 50% ethyl acetate/50% hexanes produced the product as a yellow oil (0.751 g, 100%). 1H NMR (d6-DMSO) 1.36 (9H, s), 1.44 (2H, m) 1.58 (2H, m), 2.93 (2H, m), 3.46 (2H, m), 6.82 (1H, t, J=5.6 Hz), 7.23 (1H, d, J=9.5 Hz), 8.27 (1H, dd, J=2.7 Hz, J=9.6 Hz), 8.85 (2H, m).

Provenance & Evidence