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

HRID 1861768Notes

Reaction equation

HRID 1861768 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>>[C:10]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1)(=[O:12])[CH3:11]

Participants

3

Reactant 2

HCID 37734-Piperidinecarboxylic acidHCID 7918Acetic Anhydride

Product 1

HCID 1172551-Acetylpiperidine-4-carboxylic acidYield 74%

Procedure

Isonipecotic acid (25.0 g, 0.19 mol) was dissolved in acetic anhydride (100 mL) and the solution stirred at reflux for 8 h, then the solvent was removed under reduced pressure and the crude compound crystallized from MeOH/ether to afford the title compound as a white solid (24.4 g, 74%). m.p. 171° C. 1H NMR (DMSO): 1.2-1.5 (m, 2H), 1.65-1.85 (m, 2H), 1.942 (s, 3H), 2.35-2.5 (m, 1H), 2.641 (t, J=11.7Hz, 1H), 3.038 (t, J=11.7Hz, 1H), 3.69 (d, J=13.5Hz, 1H), 4.15 (d, J=13.2Hz, 1H), 12.22 (bs, 1H). IR (KBr): 1721, 1613, 1316, 1202 (cm−1). MS (m/z): 171, 128, 82.

Workup

  1. temperatureat reflux for 8 h
  2. customthe solvent was removed under reduced pressure
  3. customthe crude compound crystallized from MeOH/ether

Sources & evidence

ORD record
ord-5d01302e7d8d485f8a741e9a24fc4ffd
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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