Triethylamine → Genz-10850

Participants

Reaction Steps

Indole-5-carboxylic acid (17 mg, 0.11 mmole) and N-9-fluorenyl-piperazine dihydrochloride (32 mg, 0.1 mmole) were dissolved in 5 ml dichloromethane. To this solution was added triethylamine (2 eq. to neutralize HCl salt), catalytic DMAP and EDCI (33 mg, 0.11 mmole). The resulting mixture was stirred at room temperature overnight and was then worked up by washing sequentially with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride. The product was then purified by flash chromatography on silica gel (40:1 CHCl3/MeOH). 1H NMR (300 Mhz, CDCl3) δ 8.38 (s, 1H), 7.72-7.60 (m, 5H), 7.40-7.18 (m, 7H), 6.55 (d, 1H), 4.88 (s,1H), 3.60 (bs, 4H), 2.62 (bs, 4H).

Provenance & Evidence