Hydrochloric Acid → Ethyl 4-methylpiperidine-3-carboxylate

HRID 931301Notes

Reaction equation

HRID 931301 reaction equation
Cl.[CH3:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH:4]1[C:9]([OH:11])=[O:10].[CH2:12](O)[CH3:13]>C(O)(=O)C>[CH3:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH:4]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 136586094-Methylpiperidine-3-carboxylic acid

Product 1

HCID 13658603Ethyl 4-methylpiperidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Hydrogen chloride gas was bubbled into a solution of 4-methylpiperidine-3-carboxylic acid (6.0 g, 41.90 mmol) in ethanol (150 mL) and acetic acid (30 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was heated at reflux for 48 h, then was cooled and was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford ethyl 4-methylpiperidine-3-carboxylate (5.0 g). The material was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 48 h
  3. temperaturewas cooled
  4. customwas partitioned between water and ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-915fa440dfb3481ebc20e592cac4db4c
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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