반응 #1721763

반응 방정식

water

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

hydroxybenzotriazole

8-chloro-6,11-dihydro-11-(1-piperazinyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

urocanic acid

→

title compound

1-(8-Chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-4-[(E)-3-(1H-imidazol-4-yl)-1-oxo-2-propenyl]piperazine

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.DISSOLUTIONdissolved (˜10 min.)
2. 2
   workup.STIRRINGto stir at room temperature for 18.5 h
3. 3
   workup.STIRRINGthe solution was stirred briefly
4. 4
   농축before concentrating under reduced pressure
5. 5
   기타The residual oil was partitioned between dichloromethane (100 mL) and water (100 mL)
6. 6
   추출The organic extract
7. 7
   건조was dried by filtration through anhydrous magnesium sulfate and solvent
8. 8
   기타removed under reduced pressure
9. 9
   기타The residue was chromatographed on silica gel
10. 10
    세척eluting with dichloromethane-methanol-concentrated ammonium hydroxide (90:9:0.5)

실험 절차

To a suspension of urocanic acid (1.38 g; 10.0 mmol) (from Aldrich Chemicals) in N,N-dimethylformamide (175 mL) under an inert atmosphere, was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.92 g; 10.0 mmol) and hydroxybenzotriazole (1.08 g; 8 mmol). The resultant mixture was warmed to 40° C. and stirring continued until all solids dissolved (˜10 min.). To the resultant solution was added 8-chloro-6,11-dihydro-11-(1-piperazinyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (8) (2.51 g; 8.0 mmol), and the resultant solution was allowed to stir at room temperature for 18.5 h. Then water (250 microliters; 13.9 mmol) was added, and the solution was stirred briefly before concentrating under reduced pressure. The residual oil was partitioned between dichloromethane (100 mL) and water (100 mL). The organic extract was dried by filtration through anhydrous magnesium sulfate and solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with dichloromethane-methanol-concentrated ammonium hydroxide (90:9:0.5), to obtain the title compound as a yellow powder that decomposed to a frothy gum at 160° C. SIMS: 434 (MH+; 50%).

출처