4-Methylnicotinic acid Hydrochloride → 4-Methylpiperidine-3-carboxylic acid

HRID 1969771

Reaction equation

HRID 1969771 reaction equation
Cl.[CH3:2][C:3]1[C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=[CH:5][CH:4]=1.[H][H]>O=[Pt]=O.CC(O)=O>[CH3:2][CH:3]1[CH2:4][CH2:5][NH:6][CH2:7][CH:8]1[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 27965064-Methylnicotinic acid HydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 136586094-Methylpiperidine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent2×

Procedure

AcOH (380 mL) was added to 4-methylnicotinic acid hydrochloride (50.5 g, 291 mmol, Maybridge) and PtO2 (5.05 g, 22.2 mmol, Johnson Matthey) in a 600 mL stainless steel reactor. The mixture was stirred under 220 psi of hydrogen at ambient temperature for about 14 hr. The supernatant solution was filtered through a nylon membrane and rinsed with enough AcOH until only the catalyst remained. The filtrate was concd under reduced pressure to give a clear oil that solidified upon cooling to ambient temperature to give crude 4-methylpiperidine-3-carboxylic acid with AcOH as an excipient (88.94 g, 170%): LC/MS (Table 1, Method b) Rt=0.44 min; MS m/z: 144 (M+H)+.

Workup

  1. filtrationThe supernatant solution was filtered through a nylon membrane
  2. washrinsed with enough AcOH until only the catalyst
  3. customto give a clear oil that

Sources & evidence

ORD record
ord-683763b43ab047b0854bd0249ed5ebf2
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Linked notes

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