Hydrochloric Acid → HCID 131729070, compound

HRID 1942290Notes

Reaction equation

HRID 1942290 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).

Workup

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

Sources & evidence

ORD record
ord-1a862328a8284ca89b7b9bba15a94b92
Source dataset
uspto-grants-2013_03
Patent number
US08389547B2

Reaction notes

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