反应详情

温度

80 °C

4-(3-hydroxy-2-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (1.00 g, 3.09 mmol) was charged to a 250 mL round bottom flask containing 10% Pd/C, stir bar and septum. Under a positive stream of N2, 2-propanol (80 mL) was added via syringe. The flask was evacuated and fitted with a balloon containing H2 and stirred, under H2, at room temperature for 18 h. LC-MS indicated only aniline present. 4-tert-Butyl-benzaldehyde (800 μL, 4.64 mmol) was added, the balloon was replaced with an air condenser and the stirring solution was heated to 80° C. for 48 h. The reaction was cooled to room temperature and filtered through celite to remove the catalyst and the solvent removed in vacuo to give a brown oil. This oil was adsorbed onto silica and purified by column chromatography, eluting with 11% ethyl acetate in hexane to afford the product as a clear waxy material (1.09 g, 81%). Mass Spectrum (+ESI): 436 [M+H]+.

1. customThe flask was evacuated
2. customfitted with a balloon
3. additioncontaining H2
4. stirringstirred, under H2, at room temperature for 18 h
5. customthe balloon was replaced with an air condenser
6. temperatureThe reaction was cooled to room temperature
7. filtrationfiltered through celite
8. customto remove the catalyst
9. customthe solvent removed in vacuo
10. customto give a brown oil
11. custompurified by column chromatography
12. washeluting with 11% ethyl acetate in hexane