Methyl Isocyanate → HCID 18545964, compound

Participants

Reaction Steps

To a solution of 6-chloro-3-[1-[2-(2,3-dihydro-1H-indol-3-yl)ethyl]-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole, oxalate 30a, as the free base, (3.6 g) in dichloromethane (100 ml) was added methylisocyanate (1.4 g) in dichloromethane (20 ml). The mixture was stirred at room temperature for 16 h, and the solvent was removed in vacuo. The residue was purified on silica gel eluted with ethyl acetate-ethanol-triethylamine (90:10:5) to give the crude product, which was recrystallized (methanol-ethyl acetate-ether) to give the title compound (1.8 g). 1H NMR (DMSO-d6) δ 1.60-1.70 (m, 1H), 1.95-2.05 (m, 1H), 2.40-2.60 (m, 4H), 2.60-2.75 (m, 5H), 3.15 (q, 2H), 3.35-3.50 (m, 1H), 3.55-3.65 (m, 1H), 4.00 (t, 1H), 6.10 (broad s, 1H), 6.55 (d, 1H), 6.85 (t, 1H), 7.05 (d, 1H), 7.10 (t, 1H), 7.20 (d, 1H), 7.45 (s, 2H), 7.80 (d, 1H), 7.85 (d, 1H), 11.25 (broad s, 1H). MS m/z (%): 437, 435 (MH+, 2%, 6%), 201 (54%), 189 (100%), 144 (64%).

Provenance & Evidence