Hydrochloric Acid → 2-[N-(tert-butoxycarbonylmethyl)amino]benzophenone

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Reaction Steps

A mixture of 2-aminobenzophenone (20.00 g, 0.101 mol), potassium iodide (8.42 g, 0.0507 mol), potassium carbonate (21.02 g, 0.152 mol), N,N-dimethylformamide (30 ml) and t-butyl bromoacetate (29.67 g, 0.152 mol) was stirred at room temperature, and allowed to react at 80° C. for 5.5 hr. The mixture was cooled to give slurry, to which 40% aqueous methylamine solution (11.81 g, 0.152mol) was added to decompose excess t-butyl bromoacetate. To the mixture were added ethyl acetate (60 ml) and 6.4% hydrochloric acid (147 g, 0.259 mol) for partition. The ethyl acetate layer was washed once with 2.1% sodium hydrogencarbonate (41 g, 0.010 mol) and condensed under reduced pressure to remove the solvent. The residue was crystallized from n-hexane (70 ml) to yield 2-[N-(tert-butoxycarbonylmethyl)amino]benzophenone (27.41 g, yield 86.8%) as a yellow crystal. (Reference value, mp: 88° C. (DSC).) 1H-NMR 200 MHz (CDCl3) δ: 1.50 (s, 9 H), 3.96 (d, J=5.3,2 H), 6.55-6.65 (m, 2H), 7.33-7.66 (m, 7H)), 8.90 (t, J=5.3,1 H) ##STR12##

Provenance & Evidence