Water → HCID 178419895, compound

Participants

Reaction Steps

A solution of (4,5-dihydro-1H-benzo[g]indazol-3-ylmethyl)-trimethylammonium iodide (0.40 g), 1,2,3,4-tetrahydroisoquinoline (0.20 cm3) and diisopropylethylamine (0.28 cm3) in DMF (10 cm3) was heated under argon at 80° C. for 24 hours, then stirred at room temperature for 48 hours. The mixture was poured into water (30 cm3) and extracted with ethyl acetate (2×20 cm3). The organic extracts were dried (MgSO4), filtered and concentrated. Flash column chromatography on silica gel, eluting with 5% ethanol-ethyl acetate, gave a yellow oil that crystallised on standing. The material was recystallised from ethyl acetate-hexane to give the title compound (0.111 g; 33%) as white needles, m.p. 180°-182° C. (from EtOAc-hexane); Found: C, 79.7; H, 6.7; N, 13.1. C21H21N3 requires C, 80.0; H, 6.7; N, 13.3%. δH (360 MHz; CDCl3) 2.72-2.80 (4H, m, 2 x --CH2 --), 2.90-2.98 (4H, m, 2 x --CH2 --), 3.70 (2H, s, --CH2N), 3.73 (2H, s, --CH2N), 6.99 (1H, d, J5.8, 1 of ArH), 7.10-7.28 (6H, m, 6 of ArH) and 7.79 (1H, d, J 7.3, 1 of ArH); m/z (CI+ ; NH3) 316 (MH+ ; 100%).

Provenance & Evidence