Hydrochloric Acid → Ethyl 1-methylpiperidine-4-carboxylate

HRID 1767750Notes

Reaction equation

HRID 1767750 reaction equation
Cl.O1CCO[CH2:4][CH2:3]1.[CH3:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]1>>[CH2:3]([O:16][C:15]([CH:12]1[CH2:13][CH2:14][N:9]([CH3:8])[CH2:10][CH2:11]1)=[O:17])[CH3:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 27369391-Methylpiperidine-4-carboxylic acid

Product 1

HCID 11062856Ethyl 1-methylpiperidine-4-carboxylateYield 499.5%

Procedure

A solution of 2N hydrochloric acid in dioxane (2.8 ml, 11.13 mmol) was added to 1-methyl-4-piperdine carboxylic acid (20 g, 111.33 mmol) and the mixture heated at reflux for 18 hours. The reaction was concentrated to dryness and the resultant solid dissolved in dichloromethane and washed with a saturated solution of sodium bicarbonate, dried (magnesium sulphate) and concentrated to afford 1-methyl-4-piperdine carboxylic acid ethyl ester as a white solid (9.52 g, 50% yield).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 hours
  3. concentrationThe reaction was concentrated to dryness
  4. dissolutionthe resultant solid dissolved in dichloromethane
  5. washwashed with a saturated solution of sodium bicarbonate
  6. dry with materialdried (magnesium sulphate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c11402bcb9024ad99ae2a447c41fc289
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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