Reacción #170824

Ecuación de reacción

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

Disolventes

ammonium chloride

ethyl acetate

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGto stir for 5 hours before it
2. 2
   Temperaturawas cooled to room temperature
3. 3
   LavadoThe organic phase was washed with saturated ammonium chloride twice
4. 4
   Secadodried over magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe crude material was purified via silica gel chromatography for 50% ethyl acetate/hexanes to 100% ethyl acetate
8. 8
   OtroPurification
9. 9
   Otroafforded white solid as the product

Procedimiento

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

Fuente