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Ammonium Chloride → 1,4-Dibenzyl-2-ethenylpiperazine

HRID 352797
ノート
印刷プレビュー

反応式

HRID 352797 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1C(OCC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[CH2:27]([Al+]CC(C)C)[CH:28](C)C.[Cl-].[NH4+].[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC>C(Cl)Cl.O1CCCC1.C(OCC)C.CCCCCC>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH:27]=[CH2:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 5

HCID 25517Ammonium Chloride2 回HCID 638159Methyltriphenylphosphonium iodideHCID 2736402Ethyl 1,4-dibenzylpiperazine-2-carboxylateHCID 21225700DiisobutylaluminumhydrideHCID 178418339Butyllithium

生成物 1

HCID 111621581,4-Dibenzyl-2-ethenylpiperazine

試薬・触媒・溶媒

4
HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒2 回

反応条件

温度
-78 °C

実験手順

After a solution of 1,4-dibenzyl-2-(ethoxycarbonyl)piperazine (6.76 g) in methylene chloride (250 ml) was cooled to −78° C., diisobutylaluminum hydride (a 1.0 mol/l hexane solution, 39.90 ml) was added dropwise and the mixture was stirred at −78° C. for 2 hours. A saturated aqueous solution of ammonium chloride and methylene chloride were added to the reaction mixture. 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 (150 ml) of methyltriphenylphosphonium iodide (8.07 g) to −78° C., n-butyl lithium (a 1.52 mole hexane solution, 13.14 ml) was added dropwise and the mixture was stirred at −78° C. for 2 hours. A solution of the residue, which residue had been obtained above, in tetrahydrofuran was then added. The reaction mixture was heated from −78° C. to 0° C. while stirring for 4 hours and then, a saturated aqueous solution of ammonium chloride was added to terminate the reaction. Diethyl ether 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 was subjected to chromatography on a silica gel column (methanol:methylene chloride=1:50), whereby the title compound (3.22 g) was obtained as a pale yellow oil.

後処理

  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. stirringthe mixture was stirred at −78° C. for 2 hours
  8. additionwas then added
  9. temperatureThe reaction mixture was heated from −78° C. to 0° C.
  10. stirringwhile stirring for 4 hours
  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
  18. customwas obtained as a pale yellow oil

出典と根拠

ORDレコード
ord-e2b7a2f4877e44a7be4439fa03d56cbd
出典データセット
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06747023B1

反応ノート

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