반응 #10084

반응 방정식

3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione

chloroacetyl chloride

→

product

수율 92.1%

N-[2-(2,6-dioxo(3-piperidyl))-1-oxoisoindolin-4-yl]-2-chloroacetamide

수율 92.1%

용매

THF

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도to reflux for 45 minutes
3. 3
   온도The reaction mixture was heated
4. 4
   온도at reflux for an additional 30 minutes
5. 5
   기타The solvent was evaporated in vacuo
6. 6
   여과filtered

실험 절차

To a stirred suspension of 3-(4-amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione (3.89 g, 15.0 mmol) in THF (50 ml) was added chloroacetyl chloride (1.86 g, 16.5 mmol). The mixture was heated to reflux for 45 minutes. To the reaction mixture was added additional chloroacetyl chloride (0.15 g, 0.13 mmol). The reaction mixture was heated at reflux for an additional 30 minutes. The solvent was evaporated in vacuo and the resulting solid was slurried in diethyl ether (20 ml) and filtered to give 4.64 g (92%) of product as an off-white solid: 1H NMR (DMSO-d6) δ 11.04 (s, 1H), 10.22 (s, 1H), 7.82 (dd, J=1.6 and 7.2 Hz, 1H), 7.59–7.50 (m, 2H), 5.16 (dd, J=5.1 and 13.2 Hz, 1H), 4.46–4.30 (m, 4H), 3.00–2.85 (m, 1H), 2.65–2.58 (m, 1H), 2.44–2.28 (m, 1H), 2.06–2.01 (m, 1H).

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