Hydrochloric Acid → Ethyl 6-methylpiperidine-3-carboxylate

HRID 1019660Notes

Reaction equation

HRID 1019660 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.Cl.[OH-].[Na+].[CH3:14][CH2:15]O>O>[CH3:1][CH:2]1[NH:7][CH2:6][CH:5]([C:8]([O:10][CH2:14][CH3:15])=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 136586116-Methylpiperidine-3-carboxylic acid

Product 1

HCID 13658605Ethyl 6-methylpiperidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 194.1 (1044 mg, 7.29 mmol) in EtOH (5207 μL) was added concentrated hydrochloric acid (405 μL, 7.29 mmol). The resulting solution was heated at reflux for 18 hours. The reaction mixture was then cooled to room temperature and poured onto water. The reaction was brought to pH 10 with 1N sodium hydroxide in water and was then extracted with EtOAc. The organic phase was then dried over anhydrous Na2SO4 and filtered to provide ethyl 6-methylpiperidine-3-carboxylate. ESI-MS M+H 172.2.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 18 hours
  3. additionpoured onto water
  4. extractionwas then extracted with EtOAc
  5. dry with materialThe organic phase was then dried over anhydrous Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-0bb690bac5c14fe995633729d8984e73
Source dataset
uspto-grants-2014_05
Patent number
US08716281B2

Reaction notes

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