Formaldehyde → 1,4-Dimethylpiperidine-4-carboxylic acid

HRID 1770099Notes

Reaction equation

HRID 1770099 reaction equation
[CH3:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:11]=O>O.[Pd]>[CH3:11][N:5]1[CH2:6][CH2:7][C:2]([CH3:1])([C:8]([OH:10])=[O:9])[CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 221045794-Methylpiperidine-4-carboxylic acid

Product 1

HCID 200954091,4-Dimethylpiperidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

4-Methyl isonipecotic acid (5.10 g, 35 mmol) was placed in a Parr flask and diluted with 400 mL H2O. 10 mL of a 30% formaldehyde solution was added followed by 5.0 g of 10% Pd/C. The reaction mixture was hydrogenated at 50 psi overnight, filtered through celite, washed with H2O, and evaporated. HPLC 1:1 methanol/dichloromethane containing 2% acetic acid afforded 1,4-dimethylpiperidine-4-carboxylic acid. (0.859 g, 15%). 1H NMR (200 MHz DMSO d6) δ3.0 (m, 2H), 2.5 (m, 2H), 2.4 (s, 3H), 2.1 (m, 2H), 1.5 (m, 2H), 1.1 (s, 3H).

Workup

  1. customwas hydrogenated at 50 psi overnight
  2. filtrationfiltered through celite
  3. washwashed with H2O
  4. customevaporated

Sources & evidence

ORD record
ord-235c10cf27644496b0abbc9c19c000e1
Source dataset
uspto-grants-1995_01
Patent number
US05385908

Reaction notes

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