Ethyl 4-piperidinecarboxylate → 4-Piperidinecarboxylic acid

HRID 235668Notes

Reaction equation

HRID 235668 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-a96305d184c547098d635fbc7f8da964
Source dataset
uspto-grants-1987_02
Patent number
US04640925

Reaction notes

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