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

HRID 972913Notes

Reaction equation

HRID 972913 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.[CH3:10][C:11](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:12]>>[C:11]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1)(=[O:12])[CH3:10]

Participants

3

Reactant 2

HCID 37734-Piperidinecarboxylic acidHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

Product 1

HCID 1172551-Acetylpiperidine-4-carboxylic acid

Procedure

The mixture of 100 g of isonipecotic acid and 40 ml of acetic anyhydride is refluxed for 2 hours and then allowed to stir at room temperature overnight. The reaction mixture is then evaporated under reduced pressure and the residue triturated with diethyl ether. The resulting solids are recrystallized from a mixture of isopropanol and diethyl ether to afford the N-acetyl isonipecotic acid, melting at 175°.

Workup

  1. temperatureanyhydride is refluxed for 2 hours
  2. customThe reaction mixture is then evaporated under reduced pressure
  3. customthe residue triturated with diethyl ether
  4. customThe resulting solids are recrystallized from a mixture of isopropanol and diethyl ether

Sources & evidence

ORD record
ord-1ae45abe938c45ea8386d6d7a348e5ef
Source dataset
uspto-grants-1977_10
Patent number
US04054570

Reaction notes

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