4-Nitrobenzyl chloride → 4-(Diphenylmethyl)-1-[(4-nitrophenyl)methyl]piperidine

HRID 258821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 258821
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[N+:26]([C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1)([O-:28])=[O:27]>C(O)C.O>[N+:26]([C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:11]2[CH2:10][CH2:9][CH:8]([CH:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:13][CH2:12]2)=[CH:31][CH:30]=1)([O-:28])=[O:27]

Komponenten

6

Edukt 3

HCID 74824-Nitrobenzyl chlorideHCID 10340Sodium CarbonateHCID 882784-Benzhydrylpiperidine

Produkt 1

HCID 214248404-(Diphenylmethyl)-1-[(4-nitrophenyl)methyl]piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 126 parts of 4-(diphenylmethyl)piperidine in 1200 parts of 95% ethanol is added a solution of 69 parts of sodium carbonate in 1500 parts of water. The resultant mixture is heated at the boiling point under reflux with vigorous stirring while a solution of 112 parts of 4-nitrobenzyl chloride in 800 parts of 95% ethanol is rapidly stirred in, and for 4 hours thereafter. Solvent is then removed by vacuum distillation, and the residue is partitioned between dichloromethane and water. The organic layer is separated, dried over anhydrous potassium carbonate, and stripped of solvent by vacuum distillation. The residue, recrystallized from anhydrous ethanol, affords 1-[(4-nitrophenyl)methyl]-4-(diphenylmethyl)piperidine melting at approximately 130°-131°.

Aufarbeitung

  1. temperatureunder reflux
  2. customSolvent is then removed by vacuum distillation
  3. customthe residue is partitioned between dichloromethane and water
  4. customThe organic layer is separated
  5. dry with materialdried over anhydrous potassium carbonate
  6. distillationstripped of solvent by vacuum distillation
  7. customThe residue, recrystallized from anhydrous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-ebe4929252fc4946b215cba8f37f8399
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04035372

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