تفاعل #10077

معادلة التفاعل

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

pentanoyl chloride

→

product

المردود 85.3%

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

المردود 85.3%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe stirred mixture was heated
2. 2
   درجة الحرارةto reflux for 18 hours
3. 3
   أخرىThe solvent was evaporated in vacuo
4. 4
   ترشيحfiltered

الإجراء التجريبي

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 pentanoyl chloride (0.48 g, 4.0 mmol). The stirred 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 (85%) of product as an off-white solid: mp 178–179° C.; 1H NMR (DMSO-d6) δ 11.17 (s, 1H), 9.65 (s, 1H), 8.50 (d, J=8.3 Hz, 1H), 7.82 (t, J=7.5 Hz, 1H), 7.59 (d, J=7.2 Hz, 1H), 5.18 (dd, J=5.0 and 12.4 Hz, 1H), 2.99–2.89 (m, 1H), 2.68–2.45 (m, 4H), 2.13–2.09 (m, 1H), 1.69–1.57 (m, 2H), 1.44–1.30 (m, 2H), 0.92 (t, J=7.2 Hz, 3H); 13C NMR (DMSO-d6) δ 172.72, 171.99, 169.73, 167.83, 166.64, 136.64, 136.07, 131.36, 125.96, 118.15, 116.68, 48.97, 36.32, 30.97, 26.88, 22.03, 21.70, 13.64; Anal. Calcd. For C19H19N3O5: C, 60.50; H, 5.36; N, 11.76. Found: C, 60.10; H, 5.37; N, 11.58.

المصدر