Reacción #449035

Ecuación de reacción

potassium carbonate

2,6-Difluoro-3-nitropyridine

1-benzyl-4-ethylaminopiperidine

acetonitrile

→

title compound

1-Benzyl-4-[N-ethyl-N-(6-fluoro-3-(nitro)-2-pyridinyl)amino]piperidine

Disolventes

( 25/75 )

ethyl acetate hexane

ethyl acetate hexane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction is slowly warmed to 20°-25°
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   LavadoThe organic phase is washed with saline
4. 4
   Secadodried over sodium sulfate
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroPurification via flash column chromatography (5% ethyl acetate/hexane to 10% ethyl acetate/hexane)

Procedimiento

2,6-Difluoro-3-nitropyridine (Recl. Trav. Chim., 95, 127-156 (1976) and Tetrahedron Lett., 28, 111-114 (1987), 2.4 g, 15.0 mmol) and 1-benzyl-4-ethylaminopiperidine (EXAMPLE 11, 3.3 g, 15 mmol) are dissolved in 37.5 mmol of acetonitrile at 0°. Then solid potassium carbonate (2.49 g, 18 mmol) is added and the reaction is slowly warmed to 20°-25°. After the reaction is complete by TLC (ethyl acetate/hexane, (25/75)), it is poured into water and extracted with ethyl acetate. The organic phase is washed with saline, dried over sodium sulfate and concentrated under reduced pressure. Purification via flash column chromatography (5% ethyl acetate/hexane to 10% ethyl acetate/hexane) gives the title compound, mp=99°-100°; NMR (300 MHz, CDCl3) 8.00, 7.13-7.04, 6.02, 3.43, 3.31, 3.28, 2.77, 1.85, 1.71, 1.63 and 0.86δ; CMR (75 MHz, CDCl3) 163.5, 160.2, 151.2, 140.9, 130.4, 128.9, 128.0, 126.9, 96.9, 62.6, 59.6, 52.9, 38.7, 29.3 and 14.0δ.

Fuente