4-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridinium chloride → 4-(4-chlorophenyl)piperidine Hydrochloride

HRID 856052Notes

Reaction equation

HRID 856052 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)=[CH:5][CH:4]=1.[H][H]>C(O)C.[Pt]=O>[ClH:2].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 27236124-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridinium chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 27578434-(4-chlorophenyl)piperidine HydrochlorideYield 188.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride (2 g, 8.7 mmol) and platinum oxide (100 mg) in ethanol (100 ml) was stirred at room temperature under an atmospheric pressure of hydrogen. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting precipitates by treating the residue with diethyl ether were collected by filtration to afford 4-(4-chlorophenyl)piperidine hydrochloride (1.9 g, yield 94%) as a pale gray powder.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting precipitates
  4. additionby treating the residue with diethyl ether
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-986537e547394dc19eb3469893a6a1b0
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…