반응 #704185

반응 방정식

1-[4,4-bis(p-fluorophenyl)-2-cyclohexenyl]-4-piperidone

ammonium chloride

3-trifluoromethyl-4-chloro-1-bromobenzene

magnesium

iodine

→

1-[4,4-bis(p-fluorophenyl)-2-cyclohexenyl]-4-(4-chloro-3-trifluoromethylphenyl)-4-piperidinol hydrochloride

용매

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition
2. 2
   온도under reflux for an additional hour
3. 3
   workup.ADDITIONis added dropwise to the reaction mixture
4. 4
   추출the whole is extracted with ethyl acetate
5. 5
   세척The extract is washed with water
6. 6
   건조dried over sodium sulfate
7. 7
   기타the solvent is removed
8. 8
   workup.DISSOLUTIONThe residual oil is dissolved in acetone
9. 9
   workup.ADDITIONTo the acetone solution is added 20% ethanolic hydrochloric acid
10. 10
    온도the whole is cooled
11. 11
    여과The precipitated crystals are collected by filtration
12. 12
    기타recrystallized from a mixture of methanol and acetone

실험 절차

A solution of 6.3 g of 3-trifluoromethyl-4-chloro-1-bromobenzene in 16 ml of tetrahydrofuran is added dropwise to a mixture of 0.6 g of magnesium turnings, a few crystals of iodine and 5 ml of tetrahydrofuran at room temperature with stirring by occasional cooling. After refluxing for 30 minutes, to the cooled Grignard reagent is added dropwise a solution of 7.3 g of 1-[4,4-bis(p-fluorophenyl)-2-cyclohexenyl]-4-piperidone (m.p. 112°-114° C) in 25 ml of tetrahydrofuran by occasional cooling. After the addition is complete, the resulting mixture is stirred at room temperature for 1 hour and then under reflux for an additional hour. After cooling a saturated aqueous solution of ammonium chloride is added dropwise to the reaction mixture, and the whole is extracted with ethyl acetate. The extract is washed with water and dried over sodium sulfate, and the solvent is removed. The residual oil is dissolved in acetone. To the acetone solution is added 20% ethanolic hydrochloric acid, and the whole is cooled. The precipitated crystals are collected by filtration and recrystallized from a mixture of methanol and acetone to give 1-[4,4-bis(p-fluorophenyl)-2-cyclohexenyl]-4-(4-chloro-3-trifluoromethylphenyl)-4-piperidinol hydrochloride as white crystals, melting at 252°-254° C.

출처