Réaction #10084

Équation de réaction

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

chloroacetyl chloride

→

product

Rendement 92.1%

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

Rendement 92.1%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was heated
2. 2
   Températureto reflux for 45 minutes
3. 3
   TempératureThe reaction mixture was heated
4. 4
   Températureat reflux for an additional 30 minutes
5. 5
   AutreThe solvent was evaporated in vacuo
6. 6
   Filtrationfiltered

Mode opératoire

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).

Source