Hydrochloric Acid → HCID 131729070, compound

HRID 1965934Notes

Reaction equation

HRID 1965934 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[ClH:22]>CO.O=[Pt]=O>[ClH:22].[F:20][C:2]([F:1])([F:21])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][CH:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11][NH:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 46942028HCID 46942028, compound

Product 1

HCID 131729070HCID 131729070, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl {2-[4-(trifluoromethyl)phenyl]pyridin-4-yl}acetate (6.2 g, 21 mmol), PtO2 (200 mg, 0.9 mmol) and HCl solution (4N in dioxane, 5.8 ml, 23 mmol) in MeOH (100 ml) was hydrogenated at 20 psi on a Parr® apparatus for 5 hours. The catalyst was removed by filtration and the filtrate evaporated in vacuo to give the desired piperidine as white solid (7.1 g, quant). 1H NMR (400 MHz, CD3OD) δ: 1.58-1.72 (1H, m), 1.75-1.85 (1H, m), 2.08 (1H, d, J 14.2), 2.19 (1H, t, J 14.2), 2.28-2.38 (1H, m), 2.45 (2H, d, J 6.9), 3.24-3.32 (1H, m), 3.51-3.57 (1H, m), 3.67 (3H, s), 4.46 (1H, d, J 10.2), 7.72 (2H, d, J 8.3), 7.79 (2H, d, J 8.4). The free base was obtained by treatment with NaHCO3 (aq) and extraction in to DCM. The organic extracts were dried, filtered and evaporated.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-b729985030574f0da9a2021a72dda3ab
Source dataset
uspto-grants-2013_04
Patent number
US08420622B2

Reaction notes

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