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

HRID 1826239Notes

Reaction equation

HRID 1826239 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(OCC)(=O)C>[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

4

Reactant 2

HCID 37734-Piperidinecarboxylic acidHCID 7918Acetic Anhydride

Product 1

HCID 1172551-Acetylpiperidine-4-carboxylic acidYield 89.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

Isonipecotic acid (10.0 g, 0.078 mol) and ethyl acetate (30.0 ml) were charged at room temperature. Acetic anhydride (11.9 g, 1.50 eq) was dropwise added over about 10 min. while retaining not more than 20° C. After stirring at 55±5° C. for 2 hrs., the mixture was allowed to cool to room temperature over 1 hr., ice-cooled and stirred at not higher than 10° C. for 1 hr. The precipitated crystals were collected by filtration and washed with diisopropyl ether (10 ml×2) and dried in vacuo at 50° C. to give the title compound (11.9 g, yield 89.8%) as white crystals.

Workup

  1. customwhile retaining not more than 20° C
  2. temperatureto cool to room temperature over 1 hr
  3. temperature, ice-cooled
  4. stirringstirred at not higher than 10° C. for 1 hr
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with diisopropyl ether (10 ml×2)
  7. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-488b7bc14f4643169fdc91195c6e233e
Source dataset
uspto-grants-2006_05
Patent number
US07049441B2

Reaction notes

Loading…