Hexane → 1,4-Dibenzyl-2-(2-methyl-1-propenyl)piperazine

温度

-78 °C

After cooling a methylene chloride solution (400 ml) of 1,4-dibenzyl-2-ethoxycarbonylpiperazine (19.57 g) to −78° C., diisobutylaluminum hydride (a 0.95 mole hexane solution, 121.7 ml) was added dropwise. The resulting mixture was stirred at −78° C. for 2.5 hours. A saturated aqueous solution of ammonium chloride and methylene chloride were added and then, the water layer was extracted three times. The organic layers were combined, washed with distilled water and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was provided for the subsequent reaction without purification. After cooling a tetrahydrofuran solution (300 ml) of isopropyltriphenylphosphonium iodide (25.0 g) to −78° C., n-butyl lithium (a 1.53 mole hexane solution, 37.8 ml) was added dropwise, followed by stirring at −78° C. for 30 minutes. A solution of the residue, which had been obtained above, in tetrahydrofuran was added dropwise to the reaction mixture. The resulting mixture was heated gradually from −78° C. and stirred overnight. A saturated aqueous solution of ammonium chloride was added to terminate the reaction. Ethyl acetate was added and the water layer was extracted three times. The organic layers were combined, washed with saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent under reduced pressure The residue was subjected to chromatography on a silica gel column (ethyl acetate:hexane=1:20), whereby the title compound (6.0 g) was obtained as a pale yellow oil.

1. extractionthe water layer was extracted three times
2. washwashed with distilled water
3. dry with materialdried over anhydrous sodium sulfate
4. customThe residue obtained
5. distillationby distilling off the solvent under reduced pressure
6. customwas provided for the subsequent reaction without purification
7. stirringby stirring at −78° C. for 30 minutes
8. additionwas added dropwise to the reaction mixture
9. temperatureThe resulting mixture was heated gradually from −78° C.
10. stirringstirred overnight
11. customto terminate
12. customthe reaction
13. extractionthe water layer was extracted three times
14. washwashed with saturated aqueous NaCl solution
15. dry with materialdried over anhydrous magnesium sulfate
16. customThe residue obtained
17. distillationby distilling off the solvent under reduced pressure The residue
18. customwas obtained as a pale yellow oil

ORDレコード

ord-ff3cd9f8369541d6863c8b1aec539401

出典データセット

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06747023B1