3-(3,5-Dichlorophenyl)pyridine → 3-(3,5-Dichlorophenyl)piperidine hydrochloride

HRID 77298Notes

Reaction equation

HRID 77298 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1>CO.Cl.O=[Pt]=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 1

HCID 576994213-(3,5-Dichlorophenyl)pyridine

Product 1

HCID 671227173-(3,5-Dichlorophenyl)piperidine hydrochlorideYield 196.8%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Synthesized according to General Procedure 37. A solution of 3-(3,5-dichlorophenyl)-pyridine (481 mg, 2.15 mmol) in MeOH (4.6 mL) and 2 M HCl (0.6 mL) was stirred under 60 psi of H2 in the presence of PtO2 (283 mg, 1.246 mmol) for 3 h using a Parr shaker. The reaction mixture was filtrated through Celite, and the filter cake was washed thoroughly with MeOH. The filtrate was concentrated under reduced pressure to afford 3-(3,5-dichlorophenyl)piperidine hydrochloride (564 mg, 92%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=230.3; tR=1.14 min.

Workup

  1. customSynthesized
  2. filtrationThe reaction mixture was filtrated through Celite
  3. washthe filter cake was washed thoroughly with MeOH
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-08d5f929fcaa4d88989c7855a59f2703
Source dataset
uspto-grants-2014_09
Patent number
US08841282B2

Reaction notes

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