Reaktion #430328

Reaktionsgleichung

N-Phenyl-o-phenylene diamine

2-Bromo-N-cyclopentyl-N-(4-methoxy-phenyl)-acetamide

Potassium carbonate

Potassium Iodide

→

N-Cyclopentyl-N-(4-methoxy-phenyl)-2-(6-phenylamino-cyclohexa-2,4-dienylamino)-acetamide

Ausbeute 56.9%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture is filtered
2. 2
   Sonstigethe solvent removed in vacuo
3. 3
   Waschenwashed with 1N HCl (2×50 mL), H2O (50 mL)
4. 4
   Trocknendried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe crude product is purified by flash chromatography on 50 g silica gel
8. 8
   Wascheneluted with EtOAc/Hexanes (3:17, 1 L)
9. 9
   Einengenconcentrated in vacuo

Vorschrift

2.03 g (10.7 mmol) N-Phenyl-o-phenylene diamine, 3.50 g (11.2 mmol, 1.05 equiv) 2-Bromo-N-cyclopentyl-N-(4-methoxy-phenyl)-acetamide, prepared as in Part A, 1.62 g (11.7 mmol, 1.1 equiv) Potassium carbonate, and 177 mg (1.1 mmol, 0.1 equiv) Potassium Iodide were combined in 35 mL DMF and stirred 18 h at 60° C. The reaction mixture is filtered and the solvent removed in vacuo. The residue is taken into EtOAc (150 mL), washed with 1N HCl (2×50 mL), H2O (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product is purified by flash chromatography on 50 g silica gel eluted with EtOAc/Hexanes (3:17, 1 L). Appropriate fractions were combined and concentrated in vacuo to give 2.53 g (6.09 mmol) of N-Cyclopentyl-N-(4-methoxy-phenyl)-2-(6-phenylamino-cyclohexa-2,4-dienylamino)-acetamide as a yellow oil: 1H NMR (Acetone-d6, 300 MHz) δ7.26-6.50 (m, 13H), 6.22 (d, 1H, J=7.9), 5.29 (s, br, 1H), 4.82 (m, 1H), 3.87 (s, 3H), 3.41 (d, 2H, J=4.4), 1.83 (m, 2H), 1.48 (m, 4H), 1.33 (m, 2H); TLC Rf =0.14 (EtOAc/Hexanes, 3:17).

Quelle