Triethylamine → HCID 178491966, compound

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A suspension of 2-(1-hydroxy-2-(4-(4-methoxyphenyl)-piperazin-1-yl)-ethylidene)-indan-1-one dihydrochloride (0.30 g), hydrazine monohydrate (1 cm3) and triethylamine (0.30 cm3) in 1:1 methanol-DMF (10 cm3) was stirred at room temperature under argon for 24 hours. The solution was poured into water (25 cm3) and extracted with ethyl acetate (2×25 cm3). The extracts were dried (MgSO4), filtered and concentrated. Flash column chromatography on silica gel, eluting with 2% methanol-dichloromethane, gave a yellow solid, which was recrystallised from ethanol-water to give the title compound (0.07 g; 29%) as yellow crystals, m.p. 176°-178° C. (from EtOH-H2O); δH (360 MHz, d6 -DMSO) 2.55-2.58 (4H, m, 2 x NCH2 CH2N), 3.01-3.04 (4H, m, 2 x NCH2CH2N), 3.27 (2H, s, --CH2 --, partly obscured by H2O signal), 3.58 (2H, s, --CH2N), 3.67 (3H, s, OCH3), 6.79 (2H, d, JAB 9.2, 2 of ArH), 6.87 (2H, d, JAB 9.2, 2 of ArH), 7.24 (1H, dd, J 7.4 and 7.4, 1 of ArH), 7.32 (1H, dd, J 7.4 and 7.4, 1 of ArH), 7.51 (1H, d, J 7.4, 1 of ArH), 7.59 (1H, broad d, J 7.4, 1 of ArH) and 12.58 (1H, broad s, NH); m/z (CI+ ; NH3) 361 (MH+ ; 23%), 214 (30) and 193 (100).

Provenance & Evidence