Sodium Hydroxide → 1-(Pyridin-2-yl)piperidine-4-carboxylic acid

HRID 6910Notes

Reaction equation

HRID 6910 reaction equation
[OH-].[Na+].C([O:5][C:6]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])C>O1CCOCC1>[N:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:12][CH2:13][CH:8]([C:6]([OH:7])=[O:5])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 38156184-Piperidinecarboxylic acid, 1-(2-pyridinyl)-, ethyl ester

Product 1

HCID 177503811-(Pyridin-2-yl)piperidine-4-carboxylic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium hydroxide solution (5M, 24.8 ml, 0.12 mol) was added drop wise to a solution of 3,4,5,6-tetrahydro-2H-[1,2′]-bipyridinyl-4-carboxylic acid ethyl ester (5.8 g, 24 mmol)(see reference Farmaco, 1993, 48(10), 1439) in 1,4-dioxane (100 ml). The mixture was stirred at room temperature for 72 hours and then evaporated under reduced pressure. The residue was purified by ion exchange chromatography on Dowex® 50 WX8 resin using methanol and ammonium hydroxide solution in water as eluant (gradient from 0:0:100 to 0:5:95 to 5:5:90). The material obtained was triturated with diethyl ether to give the title compound (4.42 g).

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was purified by ion exchange chromatography on Dowex® 50 WX8 resin
  3. customThe material obtained
  4. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-c1defd81fa024523893967969113599f
Source dataset
uspto-grants-2006_08
Patent number
US07084145B2

Reaction notes

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