Reaktion #10104

Reaktionsgleichung

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

4-(trifluoromethyl)benzoyl chloride

→

N-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-4-trifluoromethyl-benzamide

Ausbeute 77.0%

Lösungsmittel

methanol

THF

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux for 15 h
3. 3
   SonstigeThe solvent was removed in vacuo
4. 4
   Sonstigeto give a solid
5. 5
   FiltrationThe suspension was filtered
6. 6
   Waschenwashed with ether (15 mL)

Vorschrift

A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.6 g, 2.2 mmol) and 4-(trifluoromethyl)benzoyl chloride (1 g, 4.8 mmol) in THF (20 mL) was heated to reflux for 15 h. The solvent was removed in vacuo to give a solid. The solid was slurried in methanol (20 mL) for 2 h. The suspension was filtered and washed with ether (15 mL) then methanol (15 mL) to give N-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-4-trifluoromethyl-benzamide as a white solid (750 mg, 77% yield): mp, 213–215° C.; 1H NMR (DMSO-d6) δ 2.05–2.10 (m, 1H, CHH), 2.49–2.65 (m, 2H, CH2), 2.83–2.98 (m, 1H, CHH), 5.18 (dd, J=5.2, 12.5 Hz, 1H, NCH), 7.72 (d, J=7.2 Hz, 1H, Ar), 7.90–8.02 (m, 3H, Ar), 8.16–8.19 (m, 2H, Ar), 8.49 (d, J=8.4 Hz, 1H, Ar), 10.58 (s, 1H, NH), 11.17 (s, 1H, NH); 13C NMR (DMSO-d6) δ 21.99, 30.92, 48.99, 118.88, 119.36, 119.32, 123.76 (q, JC-F=271 Hz); 125.99 (q, JC-F=3.6 Hz), 127.10 128.37, 131.54, 132.16 (q, JC-F=32 Hz), 136.00, 136.26, 13721, 164.05, 166.59, 167.65, 169.68, 172.73; Anal Calcd for C21H14N3O5F3: C, 56.64; H, 3.17; N, 9.44; F, 12.80. Found: C, 56.25; H3.05; N, 9.32; F, 12.69.

Quelle