Reaktion #170825

Reaktionsgleichung

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

Lösungsmittel

water

ethyl acetate

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGto stir overnight
2. 2
   workup.WAITAfter 18 hours
3. 3
   Temperaturthe reaction was cooled to room temperature
4. 4
   WaschenThe organic phase was washed with water
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crude material was purified via column chromatography
9. 9
   SonstigeThe purification
10. 10
    Sonstigeprovided product as a white solid

Vorschrift

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

Quelle