반응 #170866

반응 방정식

N-benzylpiperidine-4-carboxamide

1-(4-chlorobenzyl)-3-methyl-1H-indole-2-carboxylic acid

DIPEA

HATU

→

title compound

N-benzyl-1-(1-(4-chlorobenzyl)-3-methyl-1H-indole-2-carbonyl)piperidine-4-carboxamide

용매

DMF

EtOAc

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred at rt for 17 h, at which time the reaction
2. 2
   세척diethyl ether and washed with 10% aq. sodium carbonate (2×)
3. 3
   건조dried over magnesium sulfate
4. 4
   농축concentrated
5. 5
   기타The residue was purified via silica gel flash chromatography (20 g silica, 50% EtOAc/Hexanes)

실험 절차

The following was added to sequentially to DMF (3 mL): 1-(4-chlorobenzyl)-3-methyl-1H-indole-2-carboxylic acid (90 mg, 0.315 mmol), DIPEA (0.170 mL, 0.945 mmol), and HATU (144 mg, 0.378 mmol). This was allowed to stir for 30 min at rt, after which time the crude N-benzylpiperidine-4-carboxamide (˜70 mg, 0.315 mmol) was added. The reaction was stirred at rt for 17 h, at which time the reaction was diluted with 1:1 EtOAc:diethyl ether and washed with 10% aq. sodium carbonate (2×), dried over magnesium sulfate, and concentrated. The residue was purified via silica gel flash chromatography (20 g silica, 50% EtOAc/Hexanes) to afford the title compound as an oil. Yield: (77 mg, 0.153 mmol, 51%) 1H NMR (400 MHz, CDCl3) 7.59, 7.34-7.14, 7.03, 5.73, 5.57, 5.43-5.32, 4.76, 4.43, 3.77-3.64, 3.10, 2.80, 2.19-1.52

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