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

HRID 1730499Notes

Reaction equation

HRID 1730499 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 isrefluxed 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. customThe reaction mixture is then evaporated under reduced pressure
  2. customthe residue triturated with diethyl ether
  3. customThe resulting solids are recrystallized from a mixture of isopropanol and diethyl ether

Sources & evidence

ORD record
ord-5f850485e3e04b8099acae402ed28257
Source dataset
uspto-grants-1976_11
Patent number
US03992546

Reaction notes

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