Ethyl 4-piperidinecarboxylate → 4-Piperidinecarboxylic acid

HRID 1380902Notes

Reaction equation

HRID 1380902 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7]CC)=[O:6])[CH2:3][CH2:2]1.Cl.ClCCN1CCOCC1.C(=O)(O)[O-].[Na+]>>[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 37734-Piperidinecarboxylic acid

Procedure

A mixture of ethyl isonipecotate (7.85 g, 0.05 mole, N-(2-chloroethyl)morpholine hydrochloride (9.30 g, 0.05 mole) and sodium bicarbonate (12.0 g, 0.14 mole) inEtOH (250 ml) was stirred at room temperature for two hours and at reflux temperature for three hours. The reaction mixture was filtered, concentrated and the residue extracted with Et2O. The Et2O layer was concentrated to give 13.4 g (quantitative yield) of 4-piperidinecarboxylic acid, 1-[2-(4-morpholinyl)-ethyl]-, ethyl ester, NMR (CDCl3) 4.0 (t, 2H), 3.6 (m, 4H), 3.0-2.3 (m, 13H), 2.2-1.5 (m, 4H), 1.4-1.0 (t, 3H).

Workup

  1. temperatureat reflux temperature for three hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. extractionthe residue extracted with Et2O
  5. concentrationThe Et2O layer was concentrated

Sources & evidence

ORD record
ord-68daab6f559e414596495a429a119ffb
Source dataset
uspto-grants-1986_04
Patent number
US04584301

Reaction notes

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