Reaktion #170824

Reaktionsgleichung

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

Lösungsmittel

ammonium chloride

ethyl acetate

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGto stir for 5 hours before it
2. 2
   Temperaturwas cooled to room temperature
3. 3
   WaschenThe organic phase was washed with saturated ammonium chloride twice
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe crude material was purified via silica gel chromatography for 50% ethyl acetate/hexanes to 100% ethyl acetate
8. 8
   SonstigePurification
9. 9
   Sonstigeafforded white solid as the product

Vorschrift

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

Quelle