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

HRID 2308087Notes

Reaction equation

HRID 2308087 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-519d45842fa1446d949e8be2474be03c
Source dataset
uspto-grants-2004_12
Patent number
US06833457B1

Reaction notes

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