1,2-Diaminocyclohexane, trans- → HCID 20740832, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried resealable Schlenk tube was charged with CuI (40 mg, 0.210 mmol), K3PO4 (1.30 g, 6.12 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (240 μL, 2.00 mmol), 5-iodo-m-xylene (900 μL, 6.24 mmol) and 2-methoxyethyl ether (1.0 mL) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 140° C. for 24 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; chloroform—chloroform saturated with aq NH3-methanol 40:40:1; 15 mL fractions). Fractions 7-14 provided 465 mg (72% yield) of the product as a tan solid. 1H NMR (400 MHz, CDCl3): δ 6.67 (s, 1H), 6.57 (s, 2H), 3.65-3.55 (m, 1H), 2.68-2.58 (m, 1H), 2.28 (s, 12H), 2.08-1.92 (m, 2H), 1.83-1.64 (m, 2H), 1.58-1.10 (m, 6H).

Provenance & Evidence