反应 #1885074

反应方程式

2-phenyl-2,5-dihydro-pyrazolo-(4,3-c)quinolin-3-one

2-Phenyl-2,5-dihydro-pyrazolo-(4,3-c) quinolin-3-one

N,N-diisopropylethylamine

triphosgene

N,N-diisopropylethylamine

4-methylpiperidine

→

5-(4-Methylpiperidine-1-carbonyl)-2-phenyl-2,5-dihydro-pyrazolo-(4,3-c)quinolin-3-one

溶剂

methylene chloride

反应条件

后处理

1. 1
   其他The reaction was quenched by addition of aqueous sodium bicarbonate solution
2. 2
   其他The organic layer was collected
3. 3
   洗涤washed with brine solution
4. 4
   干燥dried over sodium sulfate
5. 5
   过滤filtered
6. 6
   浓缩concentrated in vacuo
7. 7
   其他The product was obtained by column chromatography

实验过程

A solution of 2-phenyl-2,5-dihydro-pyrazolo-(4,3-c)quinolin-3-one (4a) (0.261 g, 1 mM) in 2 mL of anhydrous methylene chloride was stirred with N,N-diisopropylethylamine (0.145 g, 1.2 mM) and triphosgene (0.173 g, 0.55 mM) at 0° C. for 1 hour and 25° C. for 2 hours. N,N-diisopropylethylamine (0.145 g, 1.2 mM) and 4-methylpiperidine (0.208 g, 2 mM) were added at 0° C. and the reaction mixture was stirred overnight at room temperature. The reaction was quenched by addition of aqueous sodium bicarbonate solution. The organic layer was collected, washed with brine solution, dried over sodium sulfate, filtered and concentrated in vacuo. The product was obtained by column chromatography. 1H NMR (CDCl3) δ (ppm): 1.0 (3H, d, J=6.59), 1.6 (4H,m), 1.84 (1H,m), 3.14 (1H,m), 3.30 (1H,m), 4.01, (1H,m), 4.60 (1H,m), 7.20 (1H, t, J=8.57), 7.38 (1H, m), 7.68-7.42 (4H, m), 8.18 (2H, m), 8.28 (1H, s), 8.44 (1H, d, J=8.81 Hz). m/z 387.5 (MH+).

来源