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

HRID 2308748Notes

Reaction equation

HRID 2308748 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)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 acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 300 g (2.32 mol) of isonipecotic acid and 1,200 ml of acetic anhydride is heated under reflux for 2 hours in a 4 liter reactor equipped with a mechanical stirrer, a condenser and a thermometer, and the mixture is left to stand overnight. 1 liter of diethyl ether is added to the mixture, which is starting to crystallise, the solid is filtered off and the cake is washed with diethyl ether (4×500 ml), drained and recrystallised from a 40/60 mixture of diisopropyl ether/isopropyl alcohol. 153 g are isolated in a first crop and 141 g in a second crop. The N-acetylisonipecotic acid obtained melts at 148° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours in a 4 liter reactor
  3. customequipped with a mechanical stirrer, a condenser
  4. waita thermometer, and the mixture is left
  5. customto crystallise
  6. filtrationthe solid is filtered off
  7. washthe cake is washed with diethyl ether (4×500 ml)
  8. customrecrystallised from a 40/60 mixture of diisopropyl ether/isopropyl alcohol
  9. custom153 g are isolated in a first crop and 141 g in a second crop

Sources & evidence

ORD record
ord-6de2ea397fff4ad8b4f7ce8f86864c8b
Source dataset
uspto-grants-1987_09
Patent number
US04690931

Reaction notes

Loading…