Ethanol → Ethyl 4-methylpiperidine-2-carboxylate

HRID 866904Notes

Reaction equation

HRID 866904 reaction equation
Cl.[CH3:2][CH:3]1[CH2:8][CH2:7][NH:6][CH:5]([C:9]([OH:11])=[O:10])[CH2:4]1.S(Cl)(Cl)=O.[CH2:16](O)[CH3:17]>>[CH3:2][CH:3]1[CH2:8][CH2:7][NH:6][CH:5]([C:9]([O:11][CH2:16][CH3:17])=[O:10])[CH2:4]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 219885124-Methylpiperidine-2-carboxylic acid hydrochloride

Product 1

HCID 15697772Ethyl 4-methylpiperidine-2-carboxylateYield 60%

Procedure

A solution of 13 g (0.072 mole) of 4-methyl-2-piperidine-carboxylic acid hydrochloride and 50 ml of thionyl chloride in 300 ml of ethanol was refluxed for 4 hours. At the end of this period, the solvent was evaporated under reduced pressure, and the residue was extracted with a solution of chloroform and saturated potassium carbonate solution. The chloroform layer was dried over anhydrous sodium sulfate and then chloroform was evaporated. Distillation of the residue gave 7.4 g (60%) of ethyl 4-methyl-2-piperidinecarboxylate, B.P. 76°-77° C/3 mmHg.

Workup

  1. customAt the end of this period, the solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted with a solution of chloroform and saturated potassium carbonate solution
  3. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  4. customchloroform was evaporated
  5. distillationDistillation of the residue

Sources & evidence

ORD record
ord-791762d7eef24935809e8709641fc264
Source dataset
uspto-grants-1978_07
Patent number
US04101653

Reaction notes

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