Hydrochloric Acid → 1-[(Pyridin-3-yloxy)carbonyl]piperidine-4-carboxylic acid

HRID 605816Notes

Reaction equation

HRID 605816 reaction equation
[N:1]1([C:12]([O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:13])[CH2:6][CH2:5][CH:4]([C:7]([O:9]CC)=[O:8])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C1COCC1.C(O)C>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][C:12]([N:1]2[CH2:2][CH2:3][CH:4]([C:7]([OH:9])=[O:8])[CH2:5][CH2:6]2)=[O:13])[CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 575077834-Ethyl 1-pyridin-3-yl piperidine-1,4-dicarboxylate

Product 1

HCID 574218421-[(Pyridin-3-yloxy)carbonyl]piperidine-4-carboxylic acidYield 110.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Ethyl 1-pyridin-3-yl piperidine-1,4-dicarboxylate (0.732 g) was dissolved in THF (15 ml) and ethanol (8.0 ml), and under ice cooling, an aqueous 1 M sodium hydroxide solution (3.9 ml) was dropwise added thereto. This was stirred at room temperature for 2 hours, and neutralized with 1 M hydrochloric acid (0.5 ml). The reaction liquid was concentrated under reduced pressure, methanol was added to the residue, and the precipitated salt was removed through suction filtration. The filtrate was concentrated to obtain 1-[(pyridin-3-yloxy)carbonyl]piperidine-4-carboxylic acid (0.727 g) as a colorless solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure, methanol
  3. additionwas added to the residue
  4. customthe precipitated salt was removed through suction filtration
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b1a2eac451c849009e6c43ba1db75580
Source dataset
uspto-grants-2011_03
Patent number
US07915261B2

Reaction notes

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