3-Pyridinecarboxylic acid, 4-(trifluoromethyl)- → HCID 67216944, compound

HRID 1969603Notes

Reaction equation

HRID 1969603 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=[CH:5][CH:4]=1.[H][H]>CCO.[Pd]>[F:13][C:2]([F:1])([F:12])[C@H:3]1[CH2:4][CH2:5][NH:6][CH2:7][C@H:8]1[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 67216944HCID 67216944, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(trifluoromethyl)nicotinic acid (1.50 g, 7.85 mmol) in EtOH (78 mL) was passed through an H-cube™ equipped with a ThalesNano CatCart® 10 wt % Pd/C catalyst cartridge at about 1.0 mL/min, at about 80° C., under about 1305 psi of hydrogen. After about 3 h, the solvent was removed under reduced pressure to afford cis-4-(trifluoromethyl)piperidine-3-carboxylic acid (1.55 g, 100% crude): LC/MS (Table 1, Method b) Rt=0.54 min; MS m/z: 198 (M+H)+.

Workup

  1. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-69333c4fd7f34245864da6176089ce82
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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