Ethyl Acetate → HCID 178440686, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-tert-butyl-benzene-1,2-diamine (1 g, 6.09 mmol) and valerolactone (0.67 g, 6.70 mmol, 1.1 eq.) in 4N HCl aq (5 ml) was sealed and heated for 2 h at 100° C. LCMS analysis shows remaining diamine. Completion was achieved using excess of valerolactone (˜1.3 ml, 2 eq.) heating at 100° for 4 h. The reaction was cooled to RT and basified to pH 12 with a saturated solution of Na2CO3. EtOAc (100 ml) was added and organic separated, washed with saturated solution of Na2CO3, water, brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography over silica gel, eluted with DCM-MeOH from 2% to 5% gradually to yield 1.19 g (79%) of a beige solid; MS (ESI+) for C15H22N2O m/z 1 [M+H]+, 247.15; HPLC purity 100% (ret. time, 1.42 min). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.38 (9H, s), 1.65-1.75 (2H, m), 2.00 (2H, quin, J=7.17 Hz), 2.98 (2H, t, J=7.09 Hz), 3.72 (2H, t, J=5.99 Hz), 7.31 (1H, dd, J=8.51, 1.58 Hz), 7.48 (1H, d, J=8.20 Hz), 7.56 (1H, d, J=1.26 Hz).

Provenance & Evidence