반응 #170782

반응 방정식

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

1-ethyl-3-(3-dimethylaminopropyl) carbodiimide

1-Hydroxybenzotriazole

N,N-Diisopropylethylamine

2-(p-tolyl)ethanamine

→

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)-N-(4-methylphenethyl)piperidine-4-carboxamide

용매

DCM

water

ethyl acetate

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   기타The layers were separated
3. 3
   세척the organic layer was washed with another aliquot of water
4. 4
   세척The ethyl acetate layer was washed with saturated citric acid, saturated sodium bicarbonate, and saturated sodium chloride
5. 5
   건조The organic layer was dried over magnesium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The crude material was purified in silica gel using the gradient 100% DCM to 5% 7M NH3 in methanol
9. 9
   workup.ADDITIONdiluted with 95% DCM
10. 10
    기타After purification
11. 11
    기타pure white solid was obtained

실험 절차

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.252 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (97 mg, 0.504 mmol), and 1-Hydroxybenzotriazole (68 mg, 0.504 mmol) were dissolved in 3.0 mL of DCM. The reaction was allowed to stir for 10 minutes before N,N-Diisopropylethylamine (88 μL, 0.504 mmol) and 2-(p-tolyl)ethanamine (73 μL, 0.504 mmol) were added. The reaction was allowed to stir overnight. The reaction was diluted with water and ethyl acetate. The layers were separated and the organic layer was washed with another aliquot of water. The ethyl acetate layer was washed with saturated citric acid, saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was purified in silica gel using the gradient 100% DCM to 5% 7M NH3 in methanol diluted with 95% DCM. After purification, pure white solid was obtained. Yield: 24 mg (White solid)

출처