Hydrochloric Acid → Methyl 5-[3-fluoro-4-(trifluoromethoxy)phenyl]piperidine-3-carboxylate

HRID 661260Notes

Reaction equation

HRID 661260 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([CH:22]=2)[C:18]([O:20][CH3:21])=[O:19])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].Cl.[H][H]>C(O)C.[Pt]=O>[F:1][C:2]1[CH:3]=[C:4]([CH:13]2[CH2:14][NH:15][CH2:16][CH:17]([C:18]([O:20][CH3:21])=[O:19])[CH2:22]2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:10])[F:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 58116516Methyl 5-[3-fluoro-4-(trifluoromethoxy)phenyl]nicotinateHCID 178418361HCID 178418361, compound

Product 1

HCID 58116461Methyl 5-[3-fluoro-4-(trifluoromethoxy)phenyl]piperidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 5.73 g (18.2 mmol) of the compound from Example 91A in 116 ml of ethanol was admixed with 1.11 g (0.27 mmol) of platinum oxide, and hydrogenated with 14.3 ml of concentrated hydrochloric acid solution and at RT overnight in a 3.5 bar hydrogen atmosphere. The catalyst was then filtered off through a filter layer and washed repeatedly with ethanol. The combined filtrates were concentrated under reduced pressure. Yield: 5.95 g (100% of theory)

Workup

  1. customat RT
  2. customovernight
  3. filtrationThe catalyst was then filtered off through a filter layer
  4. washwashed repeatedly with ethanol
  5. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-07c6cf641ff649aeb2adeef18a65b739
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

Loading…