4-Piperidinecarboxylic acid → 1-Acetylpiperidine-4-carboxylic acid

HRID 1601123Notes

Reaction equation

HRID 1601123 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[CH3:10][CH:11]([OH:13])C.C(OC(=O)C)C>C(OC(=O)C)(=O)C>[C:11]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)(=[O:13])[CH3:10]

Participants

4

Reactant 2

HCID 37734-Piperidinecarboxylic acidHCID 22055037Isopropanol ethyl acetate

Product 1

HCID 1172551-Acetylpiperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Piperidine-4-carboxylic acid (208 g, 1.63 moles) was dissolved in acetic anhydride and the resulting solution heated at reflux under a nitrogen atmosphere for 48 hours. The flask contents were allowed to cool then concentrated under reduced pressure to give a pale yellow oil which solidified on standing. Recrystallisation from propan-2-ol then afforded the title compound as an off white solid (160 g, 0.94 moles, 58%), mp 164-166° C. (IPA-ethylacetate), δH (300 MHz;CDCl3) 1.7 (2H, m), 2.0 (2H, m), 2.2 (3H, s), 2.6 (1H, m), 2.85 (1H, m), 3.2 (1H, m), 3.8 (1H, m), and 4.4 (1H, m).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux under a nitrogen atmosphere for 48 hours
  3. temperatureto cool
  4. concentrationthen concentrated under reduced pressure
  5. customto give a pale yellow oil which
  6. customRecrystallisation from propan-2-ol

Sources & evidence

ORD record
ord-d476159c4796495aad09f35fa1316b10
Source dataset
uspto-grants-1999_11
Patent number
US05977142

Reaction notes

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