Reacción #487566

ord-60ca9b971cfa4f578d2459eefb3cd6b1

Ecuación de reacción

Clc1ccnc2[nH]ccc12
4-chloro-1H-pyrrolo[2,3-b]pyridine
CNC1CCCN(Cc2ccccc2)C1
1-benzyl-N-methylpiperidin-3-amine
CN(c1ccnc2[nH]ccc12)C1CCCN(Cc2ccccc2)C1
orange oil
Rendimiento 130.0%
CN(c1ccnc2[nH]ccc12)C1CCCN(Cc2ccccc2)C1
N-(1-benzylpiperidin-3-yl)-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine
Rendimiento 130.0%

Condiciones de reacción

Temperatura
200°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe reaction mixture was partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (20 mL)
  2. 2
    Lavadothe organic phase was washed with sat. NaCl
  3. 3
    Otrodried

Procedimiento

A sealed melted mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.18 g, 0.0012 mol) in 1-benzyl-N-methylpiperidin-3-amine (0.50 g, 0.0024 mol) was heated to 200° C. overnight. The reaction mixture was partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (20 mL), and the organic phase was washed with sat. NaCl, then dried and was reduced under vacuum to give 500 mg of orange oil. The product was chromatographed with 7% MeOH/DCM, 0.7% NH4OH to give 192 mg of an orange oil (48.8% yield).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08741895B2uspto-grants-2014_06