Formic Acid → 1-Methylpiperidine-4-carboxylic acid

HRID 1910827Notes

Reaction equation

HRID 1910827 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[CH:10](O)=O>C=O>[CH3:10][N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 37734-Piperidinecarboxylic acid

Product 1

HCID 27369391-Methylpiperidine-4-carboxylic acidYield 18%

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

A solution of 4-piperidine carboxylic acid (1.0 g, 7.75 mmol) in a mixture of 90% formic acid (3 mL) and 37% formaldehyde solution (2 mL) was heated at reflux for 20 h. The volatiles were removed in vacuo and conc. HCl added to the residue. The reaction mixture was extracted with dichloromethane and washed with brine solution. The organic layer was dried over sodium sulfate, filtered and dried to afford 1-methyl-piperidine-4-carboxylic acid (0.20 g, 18%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. customThe volatiles were removed in vacuo and conc. HCl
  4. additionadded to the residue
  5. extractionThe reaction mixture was extracted with dichloromethane
  6. washwashed with brine solution
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-602ef7dc4a81479196961b00b78d1a03
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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