Phenol → HCID 24785530, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(4-chloro-phenyl)-3-(dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl ester (0.189 g, 0.585 mmol), 3-(4-methyl-piperazin-1-yl)-benzylamine (0.100 g, 0.487 mmol) and phenol (1.0 g) was stirred at 130° C. for 1.5 hours. The reaction mixture was allowed to cool to r.t. and MeOH (10 mL) was added. After 30 minutes the precipitate was filtered off and washed with MeOH (50 mL). The crude product was purified by flash chromathography using a mixture of EtOAc, MeOH and TEA as eluent to give the product as an off white solid. Yield: 0.079 g (30%). 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 7.60 (d, 2H, J=7.92 Hz), 7.44 (s, 1H), 7.40 (d, 2H, J=7.92 Hz), 7.22 (m, 1H), 6.92 (bs, 1H), 6.85 (d, 1H, J=7.92 Hz), 6.79 (d, 1H, J=7.46 Hz), 5.15 (s, 2H), 3.19 (m, 4H), 2.53 (m, 4H), 2.32 (s, 3H). MS (ESI+) 450.95 (M+1H+).

Provenance & Evidence