反应详情

温度

25 °C

A solution consisting of 0.51 gm. (0.005 mole) diisopropylamine in 10 ml. tetrahydrofuran is chilled in an ice: methanol bath and 3 ml. of 1.68 N butyllithium in pentane is added. To this mixture is then added a solution consisting of 1.25 gm. (0.005 mole) 4(p-chlorophenyl)-4-dimethylaminocyclohexanone (prepared in Preparation I, above) in 20 ml. tetrahydrofuran. After 5 min. stirring, 1.42 gm. methyl iodide is added. The reaction mixture is stirred for another 30 min. in the cold, and then it is allowed to warm up to 25° C. Stirring is continued for 21/2 hours when 20 ml. saturated aqueous ammonium chloride is added. Benzene is also added. The organic solvent phase is separated, washed initially with water and then with brine. The organic solvents are removed by evaporation under reduced pressure. The residue thus obtained is transferred to a chromatographic column containing 200 ml. silica gel. The chromatogram is developed with 2 liters of a mixture of 3% methanol in methylene chloride followed by 2 liters of a mixture of 5% methanol in methylene chloride. Fractions which are shown by TLC to contain product are collected and combined. The solvents are removed by evaporation under reduced pressure giving the desired 4-(p-chlorophenyl)-2-methyl-4-dimethylaminocyclohexanone. The compound is recrystallized from diethyl ether to give an analytical sample having a melting point at 110° to 111° C. This is recognized to be the cis isomer with respect to the 4-amino substituent, by NMR spectroscopy.

1. additionTo this mixture is then added a solution
2. stirringThe reaction mixture is stirred for another 30 min. in the cold, and then it
3. stirringStirring
4. custom2 hours when 20 ml
5. customThe organic solvent phase is separated
6. washwashed initially with water
7. customThe organic solvents are removed by evaporation under reduced pressure
8. customThe residue thus obtained
9. additioncontaining 200 ml
10. customare collected
11. customThe solvents are removed by evaporation under reduced pressure