2,2-Diphenylethylamine → 6-[1-(2,2-Diphenyl-ethylamino)-indan-5-yloxy]-nicotinamide

Participants

Reaction Steps

Using a method similar to Example 1, using 6-(1-oxo-indan-5-yloxy)nicotinamide (Intermediate 4, 536 mg, 2.00 mmol), 2,2-diphenylethylamine (473 mg, 2.40 mmol), Ti(iPrO)4 (1.14 g, 4.00 mmol), TiCl4 (1.0M/DCM, 4.00 ml, 4.00 mmol), and NaBH3CN (251 mg, 4.00 mmol) gives the title compound (608 mg) as a white solid. Mass spectrum (ion spray): m/z=450 (M+1); 1HNMR (CDCl3): 8.57 (s, 1H), 8.14 (d, 1H), 7.33-7.18 (m, 1H), 6.98-6.90 (m, 3H), 5.85 (br. s, 2H), 4.33-4.23 (m, 2H), 3.41-3.31 (m, 2H), 2.95 (m, 1H), 2.81 (m, 1H), 2.46 (m, 1H), 1.85 (m, 1H).

Provenance & Evidence