Formaldehyde → 1-Methylpiperidine-2-carboxylic acid

HRID 467553Notes

Reaction equation

HRID 467553 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([OH:9])=[O:8].[CH2:10]=O>C(O)=O>[CH3:10][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 849Pipecolic Acid

Product 1

HCID 4159391-Methylpiperidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Into a 25 ml 3-necked round bottom flask, was placed piperidine-2-carboxylic acid (975 mg, 7.56 mmol), HCHO (2.0 ml) and HCOOH (2.6 ml). The resulting solution was allowed to react, with stirring, for 5 hours while the temperature was maintained at reflux. The reaction progress was monitored by LCMS. The mixture was then concentrated by evaporation under vacuum using a rotary evaporator. The residue was triturated with 30 ml of Et2O to provide 1-methylpiperidine-2-carboxylic acid of as a white solid (0.5 g, 41%).

Workup

  1. customInto a 25 ml 3-necked round bottom flask, was placed
  2. customto react
  3. temperaturewas maintained
  4. temperatureat reflux
  5. concentrationThe mixture was then concentrated by evaporation under vacuum
  6. customa rotary evaporator
  7. customThe residue was triturated with 30 ml of Et2O

Sources & evidence

ORD record
ord-9fe4d9224b454ca3abf2f191ce757a97
Source dataset
uspto-grants-2014_01
Patent number
US08623871B2

Reaction notes

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