반응 #10080

반응 방정식

4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione

propanoyl chloride

→

product

수율 88.1%

N-[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]propanamide

수율 88.1%

용매

THF

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도to reflux for 18 hours
3. 3
   기타The solvent was evaporated in vacuo
4. 4
   여과filtered

실험 절차

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 propanoyl chloride (0.37 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 0.58 g (88%) of product as an off-white solid: mp 221–223° C.; 1H NMR (DMSO-d6) δ 11.15 (s, 1H), 9.65 (s, 1H), 8.50 (d, J=8.3 Hz, 1H), 7.83 (t, J=7.6 Hz, 1H), 7.60 (d, J=7.2 Hz, 1H), 5.16 (dd, J=5.2 and 12.6 Hz, 1H), 2.99–2.85 (m, 1H), 2.66–2.45 (m, 4H), 2.11–2.07(m, 1H), 1.14 (t, J=7.5 Hz, 3H); 13C NMR (DMSO-d6) δ 172.69, 172.65, 169.71, 167.79, 166.62, 136.65, 136.09, 131.35, 125.93, 118.12, 116.66, 48.91, 30.91, 29.73, 21.97, 9.13; Anal. Calcd. For C16H15N3O5: C, 58.36; H, 4.59; N, 12.76. Found: C, 58.01; H, 4.45; N, 12.61.

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