반응 #1517769

반응 방정식

2-ethynylpiperidine hydrochloride

NaOH

5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl chloride

→

(2-ethynylpiperidin-1-yl)[5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl]methanone

용매

toluene

toluene

EtOAc

반응 조건

후처리

1. 1
   온도to warm to ambient temperature
2. 2
   workup.WAITAfter 1 h
3. 3
   기타the layers separated
4. 4
   workup.ADDITIONBrine was added to the aqueous layer and it
5. 5
   추출was extracted with EtOAc
6. 6
   건조The combined organics were dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타The crude material was purified by silica gel flash chromatography
10. 10
    세척eluting with 0-60% EtOAc in hexanes

실험 절차

To a rapidly-stirred mixture of 2-ethynylpiperidine hydrochloride (329 mg, 2.26 mmol), toluene (5 mL), and 1N NaOH (4.7 mL), cooled at 0° C., was added a solution of 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl chloride (500 mg, 2.26 mmol) in toluene (8 mL) dropwise over 20 mins. The mixture was stirred at 0° C. for 20 mins, then allowed to warm to ambient temperature. After 1 h, the solution was diluted with EtOAc and the layers separated. Brine was added to the aqueous layer and it was extracted with EtOAc. The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel flash chromatography eluting with 0-60% EtOAc in hexanes to provide (2-ethynylpiperidin-1-yl)[5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl]methanone as a collapsing white foam. The compound gave a high resolution mass spectrum (ES+) m/z of 259.1553, calculated for M+H+ [C17H18N4O: 295.1553]. 1H NMR δ (ppm) (CDCl3): 7.75-7.86 (3H, m), 7.30-7.34 (1 H, m), 7.18-7.20 (1H, m), 5.76 (1H, d, J=33.6 Hz), 4.50-4.67 (1H, m), 3.20-3.31 (1H, m), 2.91-3.08 (1H, m), 2.43 (3H, s), 2.04-2.36 (1H, m), 1.64-1.91 (2H, m), 1.42-1.61 (1H, m), 1.30-1.37 (1H, m).

출처