4-Pyridineacetic acid hydrochloride → 4-Piperidineacetic acid hydrochloride

HRID 902642Notes

Reaction equation

HRID 902642 reaction equation
[ClH:1].[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1>O=[Pt]=O.C(O)(=O)C>[ClH:1].[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([OH:11])=[O:10])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 810974-Pyridineacetic acid hydrochloride

Product 1

HCID 155657754-Piperidineacetic acid hydrochlorideYield 97%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4-pyridylacetic acid hydrochloride (5 g, 28.8 mmol), glacial acetic acid (100 mL) and PtO2 (0.5 g) was hydrogenated at 50 psi overnight. The solvent was decanted from the catalyst and concentrated in vacuo. Azetroped with toluene twice then washed with ether to give 5 g (97%) of white solid. MS(ESI) 144.0 (M+H+).

Workup

  1. customwas hydrogenated at 50 psi overnight
  2. customThe solvent was decanted from the catalyst
  3. concentrationconcentrated in vacuo
  4. washAzetroped with toluene twice then washed with ether

Sources & evidence

ORD record
ord-686b68ff25b84bb083a58689adcb93dc
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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