Water → HCID 178420091, compound

Participants

Reaction Steps

A solution of (4,5-dihydro-1H-benzo[g]indazol-3-ylmethyl)-trimethylammonium iodide (0.42 g), 4-(2-furan-2-ylethyl)-1,2,3,6-tetrahydropyridine (0.20 g) and diisopropylethylamine (0.20 cm3) in DMF (10 cm3) was heated under argon at 90° C. for 24 hours. The mixture was cooled, poured into water (50 cm3) and extracted with 10% ethyl acetate-diethyl ether (2×25 cm3). The extracts were dried (MgSO4), filtered and concentrated to give a brown oil. Preparative thin layer chromatography on silica, eluting with 10% methanol-dichloromethane+1% ammonia, gave the title compound as a brown off, which was recrystallised as its half-oxalate salt from ethanol-hexane (0.083 g; 18%), m.p. 205°-208° C. (from EtOH-hexane); Found: C, 70.85; H, 6.5; N, 10.05. C23H25N3O.0.5(CO2H)2.0.2(H2O) requires C, 70.6; H, 6.5; N, 10.3%. δH (360 MHz; d6 -DMSO) 2.16 (2H, broad s, NCH2CH2), 2.27 (2H, t, J 7.7, --CH2 --), 2.67-2.73 (4H, m, 2 x --CH2 --), 2.86-2.90 (4H, m, 2 x --CH2 --), 3.22 (2H, broad s, NCH2CH=C), 3.88 (2H, broad s, --CH2N), 5.42 (1H, broad s, NCH2CH=C), 6.1 (1H, d, J 3, furyl-H3), 6.33 (1H, dd, J 3 and 2, furyl-H4), 7.18-7.29 (3H, m, 3 of ArH), 7.48 (1H, d, J 2, furyl-H5) and 7.64 (1H, d, J 6.6, 1 of ArH); m/z (CI+ ; NH3) 360 (MH+ ; 30%), 204 (50) and 174 (100).

Provenance & Evidence