Dimethylformamide → HCID 17773175, compound

Participants

Reaction Steps

To a mixture of 3-(3-(4-(4-fluorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-2H-indazole (3.1 g), dimethylformamide (30 ml) and triethylamine (2.5 ml) was dropwise added acetyl chloride (0.72 ml) under ice-cooling. The mixture was stirred as it was for 30 minutes. The reaction mixture was poured into ice water (200 ml). The mixture was extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure to give 3.4 g of an oily substance. The oil was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=1:2) to give 0.60 g of 1-acetyl-3-(3-(4-(4-fluorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-1H-indazole (component eluted later (compound A)), and 0.30 g of 2-acetyl-3-(3-(4-(4-fluorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-2H-indazole (component eluted first (compound B)). 1-Acetyl-3-(3-(4-(4-fluorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-1H-indazole (compound A: m.p. 60-61° C.); 2-Acetyl-3-(3-(4-(4-fluorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydro-2H-indazole (compound B: m.p. 104-106° C.).

Provenance & Evidence