tert-Butyl 4-n-octylphenyl(methyl)carbamate → N-methyl-4-octylaniline

Participants

Reaction Steps

A solution of the product of Step A (0.14 g; 0.44 mmol) in 60% TFA in CH2Cl2 (5 ml) was stirred for 30 min at room temperature and the mixture was diluted to 5 ml with EtOH and a few drops of concentrated HCl was added. This was evaporated to dryness under reduced pressure, kept in vacuo for 1 h and the residue was partitioned between saturated NaHCO3 (5 ml) and Et2O (15 ml). The organic phase was dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane/EtOAc 9:1) to give the title compound (0.055 g; 57%), as a creamy solid. 1H-NMR (CDCl3) 7.01 (d, 2H, J=8.2 Hz); 6.55 (d, 2H, J=8.2 Hz); 3.55 (broad s, 1H); 2.81 (s, 3H); 2.49 (t, 2H, J=7.9 Hz); 1.56 (m, 2H); 1.28 (m, 10H); 0.88 (t, 3H, J=6.8 Hz).

Provenance & Evidence