Chlorosuccinimide → 3-Chloro-12-aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamine

Participants

Reaction Steps

N-chlorosuccinimide (172 mg, 1.3 mmol) was added to a solution of 12-aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamine (150 mg, 0.86 mmol) in acetonitrile (10 mL) at 60° C. in one portion. The reaction was then heated at reflux for 5 h. The resulting mixture was concentrated, diluted with CH2Cl2 (10 mL), washed with 10% ammonium hydroxide (5 mL) and brine (5 mL) before drying over MgSO4 and filtering. Concentration and purification with silica gel chromatography (0-20% MeOH in CH2Cl2) gave 3-Chloro-12-aza-tricyclo[7.2.1.0*2,7*]dodeca-2(7),3,5-trien-4-ylamine as a brown solid (27 mg, 16%). 1HNMR (400 MHz, CDCl3) δ 6.8 (d, 1H, J=8.1 Hz), 6.6 (d, 1H, J=8.1 Hz), 4.7 (d, 1H, J=5.3 Hz), 4.0-3.8 (m, 4H), 3.2 (dd, 1H, J=16.5, 4.8 Hz), 2.5 (d, 1H, J=16.5 Hz), 2.2-2.1 (m, 2H), 1.9 (m, 1H), 1.6 (m, 1H); MS (m/e) 209 (M+1); mp 220-224° C.

Provenance & Evidence