Ethyl 4-piperidinecarboxylate → 4-Piperidinecarboxylic acid

HRID 1719604Notes

Reaction equation

HRID 1719604 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-6db692a8a2f64483af4b0bae14ce7a9f
Source dataset
uspto-grants-1985_09
Patent number
US04540780

Reaction notes

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