Benzeneacetamide, 4-chloro-alpha-(4-chlorophenyl)- → 2,2-Bis(4-chlorophenyl)ethanamine

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Reaction Steps

To a solution of 2,2-bis-(4-chloro-phenyl)-acetamide (0.50 g, 1.8 mmol) in THF (10 mL) at rt was added BH3-THF (1.0 M in THF, 4.5 mL, 4.5 mmol). The solution was heated at reflux for 2 h. The mixture was cooled in an ice bath, and the excess BH3 was quenched by careful addition of 10 mL of MeOH. HCl (2.0 M in MeOH, 5 mL) was added, and the resulting mixture was heated at reflux for 1 h. After cooling, the mixture was concentrated, and the residue was partitioned between 1 N HCl and Et2O. The acidic aqueous layer was basified with 10 N NaOH and extracted with Et2O (3×). The combined organic extracts were dried (MgSO4) and concentrated to provide the desired amine (181 mg, 38%). The amine was used without further purification. 1H NMR (400 MHz, CDCl3): 7.30-7.26 (m, 4H), 7.18-7.12 (m, 4H), 3.94 (t, J=7.5, 1H), 3.28 (d, J=7.6, 2H), 1.06 (br s, 2H).

Provenance & Evidence