Reacción #79568

Ecuación de reacción

2-chloro-N-(1,3,3-trimethylbicyclo[2,2,1]hept-2-yl)acetamide

N-cyclohexylaniline

LiHMDS

Water

→

2-(cyclohexylphenylamino)-N-(1,3,3-trimethylbicyclo[2.2.1]hept-2-yl)acetamide

Disolventes

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrorecooled to −78° C.
2. 2
   Temperaturato warm to room temperature
3. 3
   Extracciónthe mixture was extracted with ethyl acetate
4. 4
   LavadoThe organic layer was washed with brine
5. 5
   Secadodried over magnesium sulfate
6. 6
   OtroThe ethyl acetate solution was absorbed onto silica gel, which
7. 7
   Lavadowas eluted with 3% methanol/methylene chloride

Procedimiento

To a solution of N-cyclohexylaniline (100 mg, 0.56 mmol) in tetrahydrofuran (4 ml) at −78° C. was added LiHMDS (1 ml of a 1M solution in tetrahydrofuran) dropwise. The solution was allowed to warm to 0° C., then recooled to −78° C., and a solution of 2-chloro-N-(1,3,3-trimethylbicyclo[2,2,1]hept-2-yl)acetamide (124 mg, 0.56 mmol) in tetrahydrofuran (1 ml) added dropwise. The mixture was allowed to warm to room temperature, and was stirred for 1 hour. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate. The ethyl acetate solution was absorbed onto silica gel, which was eluted with 3% methanol/methylene chloride, to yield 2-(cyclohexylphenylamino)-N-(1,3,3-trimethylbicyclo[2.2.1]hept-2-yl)acetamide.

Fuente