반응 #170824

반응 방정식

N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

sodium hydride

acetic anhydride

→

1-(1-acetyl-1H-indole-2-carbonyl)-N-benzyl-N-methylpiperidine-4-carboxamide

용매

ammonium chloride

ethyl acetate

DMF

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGto stir for 5 hours before it
2. 2
   온도was cooled to room temperature
3. 3
   세척The organic phase was washed with saturated ammonium chloride twice
4. 4
   건조dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The crude material was purified via silica gel chromatography for 50% ethyl acetate/hexanes to 100% ethyl acetate
8. 8
   기타Purification
9. 9
   기타afforded white solid as the product

실험 절차

A solution of N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (100 mg, 0.266 mmol) in 1 mL of DMF was added to a suspension of sodium hydride (11.72 mg, 0.293 mmol) in 2.0 mL DMF. The reaction was stirred at 80° C. for 10 minutes before adding acetic anhydride (0.050 ml, 0.533 mmol). The reaction was allowed to stir for 5 hours before it was cooled to room temperature and diluted with ammonium chloride and ethyl acetate. The organic phase was washed with saturated ammonium chloride twice, followed by saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated. The crude material was purified via silica gel chromatography for 50% ethyl acetate/hexanes to 100% ethyl acetate. Purification afforded white solid as the product. (Yield: 13 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 8.12-8.06, 7.65-7.59, 7.41-7.13, 6.91-6.84, 4.65, 4.49, 3.96-3.83, 3.06-2.94, 2.76, 2.61-2.55, 1.87-1.49

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