Hexamethylenetetramine → 1-Amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromide

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Reaction Steps

A mixture of 1-bromo-3-(3,4-dichlorophenyl)-3-methylbutan-2-one (4.0 g, 13 mmol) and HMTA (hexamethylenetetramine, 2.0 g, 14 mmol) in DCM (25 mL) was stirred 48 h at room temperature. The volatiles were evaporated in vacuo. The crude material was dissolved in EtOH (80 mL) and combined with conc HCl (40 mL). The resulting mixture was heated at reflux 2 h, cooled to room temperature, and concentrated in vacuo to give 1-amino-3-(3,4-dichlorophenyl)-3-methylbutan-2-one hydrobromide (6.75 g), which was used in the next reaction without purification. 1H NMR (400 MHz, DMSO-d6) δ 8.00 (bs, 3H), 7.61 (d, 1H), 7.52 (d, 1H), 7.29 (dd, 1H), 3.94 (m, 2H), 1.47 (s, 6H).

Provenance & Evidence