تفاعل #79568

معادلة التفاعل

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

المذيبات

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىrecooled to −78° C.
2. 2
   درجة الحرارةto warm to room temperature
3. 3
   استخلاصthe mixture was extracted with ethyl acetate
4. 4
   غسيلThe organic layer was washed with brine
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   أخرىThe ethyl acetate solution was absorbed onto silica gel, which
7. 7
   غسيلwas eluted with 3% methanol/methylene chloride

الإجراء التجريبي

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.

المصدر