Hydrochloric Acid → HCID 58659410, compound

Participants

Reaction Steps

To a solution of (3-amino-5-trifluoromethyl-phenyl)-(4-ethyl-piperazin-1-yl)-methanone (14.6 g, 48.5 mmol) in THF (120 ml) under N2-atmosphere, a 1 M solution of BH3.THF (145.5 ml) is added dropwise (exothermic). The mixture is stirred for 14 h at rt and then 5 h at 65° C. After cooling to rt, HCl conc./H2O 1:1 (250 ml) Is added and the mixture stirred for 15 h. The suspension is filtered, the filtrate extracted 3 times with AcOEt. The organic phases are washed twice with 1 N HCl and then discarded. The combined acidic phases are made basic by addition of saturated Na2CO3 solution and extracted 3 times with AcOEt. The organic layers are washed twice with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; AcOEt/EtOH/NH3 95:5:1→90:10:1) followed by extraction between 3 portions of AcOEt, 3 portions of water and finally brine, drying (Na2SO4) and concentration yields the title compound as an oil: MS: [M+1]+=288; 1H-NMR (CDCl3): 6.94 (s, 1H), 6.82 (s, 1H), 6.78 (s, 1H), 3.82 (sb, H2N), 3.46 (s, 2H), 2.51 (m, 8H), 2.44 (q, 2H), 1.10 (t, 3H).

Provenance & Evidence