Formic Acid → Methyl 1-Methyl-4-piperidinecarboxylate

HRID 1769042Notes

Reaction equation

HRID 1769042 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[CH:11](O)=O>C=O.O>[CH3:11][N:7]1[CH2:8][CH2:9][CH:4]([C:3]([O:2][CH3:1])=[O:10])[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 424914Methyl isonipecotate

Product 1

HCID 3616844Methyl 1-Methyl-4-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 712FormaldehydeSolventHCID 962WaterSolvent

Procedure

Dissolve isonipecotic acid methyl ester in formaldehyde (19.4 mL of a 37.5% solution in water, 262 mmol) and treat with formic acid (10.2 mL of a 90% solution, 240 mmol). Heat on a steam bath for 2 hours and evaporate the solvent in vacuo. Dissolve the residue in ethyl ether, dry (MgSO4), filter and evaporate the filtrate in vacuo. Purify by distillation under an argon atmosphere to give 1-methyl-4-piperidinecarboxylic acid, methyl ester as a clear colorless oil (bp 195°-205° C., 760 mm).

Workup

  1. temperatureHeat on a steam bath for 2 hours
  2. customevaporate the solvent in vacuo
  3. dissolutionDissolve the residue in ethyl ether
  4. dry with materialdry (MgSO4)
  5. filtrationfilter
  6. customevaporate the filtrate in vacuo
  7. distillationPurify by distillation under an argon atmosphere

Sources & evidence

ORD record
ord-a78b26fd7f6649639b4f072b722cc07a
Source dataset
uspto-grants-1995_01
Patent number
US05380731

Reaction notes

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