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

HRID 269732Notes

Reaction equation

HRID 269732 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:0.88 ammonia: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); LCMS: m/z ES+ 288 [M+H]+

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-7dd20b1d65c4448caabc1c8ae1d94dab
Source dataset
uspto-grants-2008_11
Patent number
US07449462B2

Reaction notes

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