反応 #158244

反応方程式

piperidin-4-one

triethylamine

DMF

→

4-oxo-piperidine-1-carboxylic acid diethylamide

反応条件

後処理

1. 1
   その他The solvent was evaporated
2. 2
   その他the residue was partitioned in H2O
3. 3
   抽出The aqueous layer was extracted with EtOAc
4. 4
   乾燥the combined organic layers were dried over Na2SO4
5. 5
   濃縮concentrated
6. 6
   その他The crude product was purified by a CombiFlash chromatography system

実験手順

To a solution of piperidin-4-one in DMF was added triethylamine (1.5 eq.) N,N-diethylacetamide chloride (1.5 eq.). The resulting solution was stirred at room temperature for 5 hours or until completion observed by TLC. The solvent was evaporated and the residue was partitioned in H2O and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by a CombiFlash chromatography system using silica gel cartridge and CH2Cl2/MeOH gradient eluent to afford 4-oxo-piperidine-1-carboxylic acid diethylamide, which was subsequently reacted with 3-hydroxybenzaldehyde (2.5 eq.) in acetic acid (99.7%) and purged with HCl gas (0.5-1 h). After stirring at room temperature for 3 hours, the solvent was evaporated and the crude was purified by a Combiflash chromatography system with hexanes/EtOAc as eluent, followed by crystallization from MeOH, to afford Compound 12 as a yellow crystalline solid.

出典