Réaction #170825

Équation de réaction

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

sodium hydride

1-iodo-2-methylpropane

→

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

Solvants

water

ethyl acetate

DMF

DMF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGto stir overnight
2. 2
   workup.WAITAfter 18 hours
3. 3
   Températurethe reaction was cooled to room temperature
4. 4
   LavageThe organic phase was washed with water
5. 5
   Séchagedried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   AutreThe crude material was purified via column chromatography
9. 9
   AutreThe purification
10. 10
    Autreprovided product as a white solid

Mode opératoire

N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (100 mg, 0.266 mmol) was dissolved in 1.0 mL of DMF and added to a suspension of sodium hydride (12.78 mg, 0.320 mmol) in 2.0 mL of DMF. The reaction was stirred at 80° C. for 10 minutes before adding 1-iodo-2-methylpropane (0.061 mL, 0.533 mmol). The reaction was allowed to stir overnight. After 18 hours, the reaction was cooled to room temperature before diluting with water and ethyl acetate. The organic phase was washed with water followed by saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated. The crude material was purified via column chromatography using 50% ethyl acetate/hexanes to 100% ethyl acetate. The purification provided product as a white solid. (Yield: 28 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 7.64-7.51, 7.43-7.16, 7.11-7.03, 6.71-6.61, 4.67, 4.51, 4.19-4.07, 3.13-2.91, 2.79, 2.06-1.93, 1.88-1.50, 0.84-0.73

Source