1,4-Dichlorobenzene → HCID 10130354, compound

HRID 276155Notes

Reaction equation

HRID 276155 reaction equation
[CH:1]1[C:6](Cl)=[CH:5][CH:4]=[C:3]([Cl:8])[CH:2]=1.[NH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.CC[O-].[Na+]>C(O)C.O1CCOCC1>[Cl:8][C:3]1[CH:2]=[CH:1][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 46851,4-DichlorobenzeneHCID 8082PiperidineHCID 2723922Sodium ethoxide

Product 1

HCID 10130354HCID 10130354, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

15 mmol of p-dichlorobenzene (2.2 g), 15.5 mmol of piperidine (1.3 g), 15.5 mmol of NaOEt solution in ethanol (10% by weight) and 50 mg of trans-di-μ-chlorobis[2-[bis(1,1-dimethylethyl)phosphino]-2-methylpropyl-C,P]dipallium(II) are suspended in 75 ml of dioxane and refluxed for 15 hours. After aqueous work-up, extraction with petroleum ether and drying over sodium sulfate, the solvents are removed under reduced pressure. This gives crude N-(4-chlorophenyl)piperidine as a light brown liquid which can be purified by distillation (boiling point: 50° C./0.08 torr); melting point: 69° C.; yield: 59%.

Workup

  1. temperaturerefluxed for 15 hours
  2. extractionAfter aqueous work-up, extraction with petroleum ether
  3. dry with materialdrying over sodium sulfate
  4. customthe solvents are removed under reduced pressure

Sources & evidence

ORD record
ord-0a3d38878f2049c5851fcc6e859b79ed
Source dataset
uspto-grants-2002_03
Patent number
US06353136B1

Reaction notes

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