Reaktion #970355

Reaktionsgleichung

2-amino-N-benzyl-4-methylthiazole-5-carboxamide

triethylamine

3-phenylpentanedioyl dichloride

→

title compound

Ausbeute 60.0%

N-benzyl-2-(2,6-dioxo-4-phenylpiperidin-1-yl)-4-methylthiazole-5-carboxamide

Ausbeute 60.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 20% hydrochloric acid solution (20 mL)
2. 2
   Trocknendried over anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   EinengenThe filtrate was concentrated in vacuo
5. 5
   Sonstigethe residue was crystallized from ethyl acetate/hexane
6. 6
   Sonstigeto afford a solid, which
7. 7
   Waschenwas washed with cold methanol
8. 8
   Sonstigedried in air

Vorschrift

To a stirred solution of 2-amino-N-benzyl-4-methylthiazole-5-carboxamide (0.50 g, 2.0 mmol) in chloroform (15 mL) with triethylamine (1.8 mL, 10.0 mmol) was added 3-phenylpentanedioyl dichloride (0.45 g, 1.84 mmol). The mixture was stirred at ambient temperature for 2 h, washed with 20% hydrochloric acid solution (20 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was crystallized from ethyl acetate/hexane to afford a solid, which was washed with cold methanol and dried in air to afford the title compound (0.46 g, 60%): 1H NMR (300 MHz, CDCl3) δ 7.50-7.20 (m, 10H), 6.07 (br s, 1H), 4.60 (d, J=5.6 Hz, 2H), 3.60-3.50 (m, 1H), 3.13 (dd, J=17.1, 4.2 Hz, 2H), 2.95 (dd, J=17.1, 12.0 Hz, 2H), 2.68 (s, 3H); MS (ES+) m/z 420.1 (M+1).

Quelle