4-bromo-N,N-dimethylaniline → HCID 20740831, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried resealable Schlenk tube was charged with CuI (190 mg, 0.998 mmol), K3PO4 (2.10 g, 9.89 mmol), 4-bromo-N,N-dimethylaniline (1.00 g, 5.00 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (0.60 L, 5.00 mmol) and dioxane (3.0 mL) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 70 h. The resulting dark brown suspension was cooled to room temperature and filtered through a 2×1 cm pad of Celite eluting with 50 mL of dichloromethane. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×20 cm; dichloromethane saturated with aq NH3-methanol 40:1; 20 mL fractions). Fractions 12-16 provided 692 mg (59% yield) of the product as a brown solid. 1H NMR (400 MHz, CDCl3): δ 6.75-6.63 (m, 4H), 3.00 (br s, 1H), 2.87-2.77 (m, 7H), 2.53-2.45 (m, 1H, 2.17-2.04 (m, 1H), 2.02-1.94 (m, 1H), 1.78-1.16 (m, 7H), 1.04-0.92 (m, 1H). 13C NMR (100 MHz, CDCl3) δ 144.7, 140.9, 116.2, 116.1, 62.0, 56.5, 42.6, 35.7, 33.0, 25.8, 25.5.

Provenance & Evidence