Hydrochloric Acid → (+/-)-Methyl(cis)-2-[4-(trifluoromethyl)phenyl]piperidine-4-carboxylate hydrochloride

HRID 1869742Notes

Reaction equation

HRID 1869742 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1.[ClH:21]>CO.O1CCOCC1.[Pt]=O>[ClH:21].[F:19][C:2]([F:1])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:10][C@@H:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]2)=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66731996HCID 66731996, compound

Product 1

HCID 131727833(+/-)-Methyl(cis)-2-[4-(trifluoromethyl)phenyl]piperidine-4-carboxylate hydrochloride

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 2-[4-(trifluoromethyl)phenyl]isonicotinate (5 g) was dissolved in MeOH (180 ml) and HCl in dioxane (4.5 ml, 4N). To this solution was added platinum oxide (500 mg) and the mixture was hydrogenated at 30 psi for 2 h. The mixture was filtered through Hyflo® to remove the catalyst and the solution was evaporated and azeotroped with toluene to yield the product as a white crystalline solid (5 g). 1H NMR (400 MHz, CDCl3) δ: 1.95-2.03 (1H, m), 2.09-2.17 (1H, m), 2.33 (1H, d, J 14.5), 2.44 (1H, d, J 14.2), 2.95-3.02 (1H, m), 3.35-3.39 (1H, m), 3.60-3.64 (1H, m), 3.75 (3H, s), 4.51 (1H, dd, J 2.7, 12.6), 7.74 (2H, d, J 8.2), 7.83 (2H, d, J 8.2); M/Z (ES+) 288 (MH+).

Workup

  1. filtrationThe mixture was filtered through Hyflo®
  2. customto remove the catalyst
  3. customthe solution was evaporated
  4. customazeotroped with toluene

Sources & evidence

ORD record
ord-2caf45cebf7d4f80baadba9f1610250f
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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