반응 #11618

반응 방정식

sodium bicarbonate

4-nitro-benzoic acid

piperidine

→

1-(4-nitrobenzoyl)piperidine

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타A room temperature solution of 5.04 gms
2. 2
   기타1′,1′-carbonyl-diimidizole and immediately immersed in an ice bath
3. 3
   추출the resulting mixture is extracted with ethyl acetate
4. 4
   기타The organics are separated
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타subsequently evaporated to dryness in vacuo
7. 7
   기타The crude product residue is then chromatographed by flash silica gel chromatography
8. 8
   기타evaporation of solvent

실험 절차

A room temperature solution of 5.04 gms. 4-nitro-benzoic acid in tetrahydrofuran (10 mL) is treated with 5.14 gms. 1′,1′-carbonyl-diimidizole and immediately immersed in an ice bath. The reaction mixture is stirred in the ice bath for 30 minutes, then it is allowed to warm to room temperature. Once at room temperature the reaction mixture is treated with 3 mL piperidine. The reaction mixture is allowed to stir at room temperature ovenight. The reaction is then made basic with the addition of saturated aqueous sodium bicarbonate solution, and the resulting mixture is extracted with ethyl acetate. The organics are separated, dried over anhydrous sodium sulfate, and subsequently evaporated to dryness in vacuo. The crude product residue is then chromatographed by flash silica gel chromatography using 50% ethyl acetate in hexanes as the eluant. Following evaporation of solvent, 1-(4-nitrobenzoyl)piperidine is isolated as a white solid in the amount of 5.87 gms.

출처