Reaktion #1123844

Reaktionsgleichung

1,3-Dioxo-2-(1-phenethyl-2,6-dioxopiperidin-3-yl)isoindoline

N-phthaloyl-DL-glutamic anhydride

phenethylamine

→

N-phenethyl phthalimide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeisolated
2. 2
   TemperaturThe reaction mixture was cooled down
3. 3
   Sonstigepurified by column chromatography, first using petroleum ether/dichloromethane (1:5) as an eluent

Vorschrift

1,3-Dioxo-2-(1-phenethyl-2,6-dioxopiperidin-3-yl)isoindoline (8) was specifically prepared and isolated as follows. A mixture of N-phthaloyl-DL-glutamic anhydride (300 mg, 1.13 mmol) and phenethylamine (139 mg, 1.13 mmol) was stirred in a 177° C. oil bath for two hours. The reaction mixture was cooled down and purified by column chromatography, first using petroleum ether/dichloromethane (1:5) as an eluent to afford N-phenethyl phthalimide as a pale yellow solid [1H NMR (CDCl3) δ 7.78-7.77 (m, 2H), 7.65-7.62 (m 2H), 7.22-7.16 (m, 5H), 3.83 (t, 2H), 2.92 (t, 2H)], and then using dichloromethane as an eluent to afford N-phenethyl thalidomide as a syrup that was then recrystallized from ether to provide white crystals [(139 mg, 34%): mp 122-123° C.; 1H NMR (CDCl3) δ 7.84-7.81 (dd, J=3.1 Hz, J=5.4 Hz, 2H), 7.72-7.69 (dd, J=3.1 Hz, J=5.4 Hz, 2H), 7.20-7.14 (m, 5H), 4.89 (dd, J=5.4 Hz, J=12.5 Hz, 1H), 4.01-3.92 (m, 2H), 2.90-2.63 (m, 5H), 2.06-2.02 (m, 1H); Anal. Calcd for C21H18N2O4: C, 69.60; H, 5.01; N, 7.73. Found: C, 69.40; H, 5.13; N, 7.74].

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