1-Methyl-1,2,3,6-tetrahydropyridin-1-ium-5-carboxylic acid;chloride → 1-methylpiperidine-3-carboxylic Acid

HRID 840260Notes

Reaction equation

HRID 840260 reaction equation
[CH3:1][NH+:2]1[CH2:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH2:4][CH2:3]1.[Cl-]>O.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]([C:8]([OH:10])=[O:9])[CH2:7]1

Participants

4

Reactant 1

HCID 223681-Methyl-1,2,3,6-tetrahydropyridin-1-ium-5-carboxylic acid;chloride

Product 1

HCID 27369371-methylpiperidine-3-carboxylic AcidYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Arecaidine hydrochloride (4 grams) (22.6 mmoles) was hydrogenated in water (100 ml) using 10% Pd—C at 40 psi at 25° C. for 24 hours. The catalyst was filtered off and washed with water. The aqueous solution was shaken with BioRad AG1X8 resin (OH− form) (23 ml bed) and after 5 minutes the resin was filtered off and washed with water. The aqueous solution was evaporated to give the title compound (Yield: 2.95 grams, 92%).

Workup

  1. customat 25° C.
  2. customfor 24 hours
  3. filtrationThe catalyst was filtered off
  4. washwashed with water
  5. filtrationwas filtered off
  6. washwashed with water
  7. customThe aqueous solution was evaporated

Sources & evidence

ORD record
ord-e32960a44d58439abe85c92dae1c6a57
Source dataset
uspto-grants-2002_04
Patent number
US06365588B1

Reaction notes

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