Reacción #579477

Ecuación de reacción

triethylamine

N-(Chloroacetyl)-2,6-diisopropylaniline

N-pentyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine

potassium iodide

→

N-[[[(2,6-diisopropylphenyl)amino]carbonyl]methyl]-N-pentyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine

Rendimiento 33.0%

Disolventes

ethyl acetate

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThree hours later, the reaction mixture was cooled
2. 2
   Lavadothe mixture was washed four times with brine (50 mL
3. 3
   SecadoThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Concentraciónconcentrated under reduced pressure

Procedimiento

N-(Chloroacetyl)-2,6-diisopropylaniline (196.3 mg), N-pentyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine (430.0 mg), potassium iodide (70 mg) and triethylamine (0.6 g) were suspended in dimethylformamide (3 mL). The resulting mixture was heated to about 80° C., and then stirred at that temperature. Three hours later, the reaction mixture was cooled, ethyl acetate (30 mL) was added, and the mixture was washed four times with brine (50 mL, each). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column (hexane/ethyl acetate) to afford N-[[[(2,6-diisopropylphenyl)amino]carbonyl]methyl]-N-pentyl-N-[[2′-[N-(triphenylmethyl)tetrazol-5-yl]-1,1′-biphenyl-4-yl]methyl]amine (196.4 mg). Yield: 33%.

Fuente