Reacción #1181621

ord-96af17530c27410d82d9e47b838b06ca

Ecuación de reacción

N#CCc1ccc(C(F)(F)F)cc1
4-(trifluoromethyl)phenylacetonitrile
CCN(CC)CCCC(C)Nc1cc(/C=C/c2ccccc2Cl)nc2cc(Cl)ccc12
aminoquinoline
O=C[O-].[NH4+]
ammonium formate
→
FC(F)(F)c1ccc(CCNc2cnc3ccccc3c2)cc1
title compound
Rendimiento 73.0%
FC(F)(F)c1ccc(CCNc2cnc3ccccc3c2)cc1
Quinolin-3-yl-[2-(4-trifluoromethyl-phenyl)-ethyl]-amine
Rendimiento 73.0%

Reactantes

N#CCc1ccc(C(F)(F)F)cc1
4-(trifluoromethyl)phenylacetonitrile
CCN(CC)CCCC(C)Nc1cc(/C=C/c2ccccc2Cl)nc2cc(Cl)ccc12
aminoquinoline
O=C[O-].[NH4+]
ammonium formate

Reactivos

[Pd]
Pd/C

Disolventes

CO
MeOH

Condiciones de reacción

Temperatura
80°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    FiltraciónFiltration, concentration and purification by chromatography (SiO2, CH2Cl2/MeOH)

Procedimiento

A solution of 10.4 mmol 4-(trifluoromethyl)phenylacetonitrile (commercially available) and 3.5 eq. aminoquinoline in MeOH (10 mL) was treated with ammonium formate (5 eq.) and 10% Pd/C (100 mg) and stirred at 80° C. for 2 h. Filtration, concentration and purification by chromatography (SiO2, CH2Cl2/MeOH) afforded the title compound (73%) as a yellow oil. MS m/e: 317.1 [M+H]+.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08133909B2uspto-grants-2012_03