Reaktion #10084

Reaktionsgleichung

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

chloroacetyl chloride

→

product

Ausbeute 92.1%

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

Ausbeute 92.1%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturto reflux for 45 minutes
3. 3
   TemperaturThe reaction mixture was heated
4. 4
   Temperaturat reflux for an additional 30 minutes
5. 5
   SonstigeThe solvent was evaporated in vacuo
6. 6
   Filtrationfiltered

Vorschrift

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).

Quelle