Heptanoyl chloride → N-[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]heptanamide

참여 물질

반응 단계

To a stirred suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2.0 mmol) in THF (30 ml) was added heptanoyl chloride (0.59 g, 4.0 mmol). The mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo and the resulting solid was slurried in diethyl ether (20 ml) and filtered to give 0.61 g (79%) of product as an off-white solid: mp 200–202° C.; 1H NMR (DMSO-d6) δ 11.16 (s, 1H), 9.65 (s, 1H), 8.48 (d, J=8.3 Hz, 1H), 7.81 (t, J=7.7 Hz, 1H), 7.58 (d, J=7.2 Hz, 1H), 5.15 (dd, J=4.8 and 12.2 Hz, 1H), 2.97–2.87 (m, 1H), 2.65–2.43 (m, 4H), 2.10–2.06 (m, 1H), 1.61–1.58 (m, 2H), 1.28 (bs, 6H), 0.85 (bs, 3H); 13C NMR (DMSO-d6) δ 172.67, 171.96, 169.69, 167.78, 166.61, 136.62, 136.04, 131.36, 125.97, 118.13, 116.67, 48.93, 36.56, 30.95, 28.16, 24.69, 21.94, 13.84; Anal. Calcd. For C20H23N3O5: C, 62.3 3; H, 6.02; N, 10.90. Found: C, 62.14; H, 6.05; N, 10.72.

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