反応 #10080

反応方程式

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

propanoyl chloride

→

product

収率 88.1%

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

収率 88.1%

溶媒

THF

反応条件

後処理

1. 1
   温度The mixture was heated
2. 2
   温度to reflux for 18 hours
3. 3
   その他The solvent was evaporated in vacuo
4. 4
   ろ過filtered

実験手順

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.

出典