Reaction #79568

Reaction equation

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

Solvents

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   Otherrecooled to −78° C.
2. 2
   Temperatureto warm to room temperature
3. 3
   Extractionthe mixture was extracted with ethyl acetate
4. 4
   WashThe organic layer was washed with brine
5. 5
   Dryingdried over magnesium sulfate
6. 6
   OtherThe ethyl acetate solution was absorbed onto silica gel, which
7. 7
   Washwas eluted with 3% methanol/methylene chloride

Procedure

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.

Source