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

HRID 1826237Notes

Reaction equation

HRID 1826237 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]>O>[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 75.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

Isonipecotic acid (129.2 g, 1.00 mol) was dissolved in water (390 mL), and acetic anhydride (153.1 g, 1.50 mol) was added dropwise under ice-cooling for about 10 min. (dropwise addition at 15–18° C. for about 10 min.). After stirring at 55±5° C. for 2 hrs., the mixture was allowed to cool to room temperature and stirred under ice-cooling for 1 hr. The precipitated crystals were collected by filtration, washed with cold diisopropyl ether (125 mL×2) and dried under reduced pressure at 40° C. for 8 hrs. to give the title compound (129.1 g, yield 75.4%).

Workup

  1. temperaturecooling for about 10 min. (
  2. additiondropwise addition at 15–18° C. for about 10 min.)
  3. temperatureto cool to room temperature
  4. stirringstirred under ice-
  5. temperaturecooling for 1 hr
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with cold diisopropyl ether (125 mL×2)
  8. customdried under reduced pressure at 40° C. for 8 hrs

Sources & evidence

ORD record
ord-166685f92a964bbc87a4ddc4cc8093c3
Source dataset
uspto-grants-2006_05
Patent number
US07049441B2

Reaction notes

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