Hydrochloric Acid → 5-Morpholinopicolinic acid

HRID 2404263Notes

Reaction equation

HRID 2404263 reaction equation
N1([C:7]([C:9]2[N:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[O:8])CCCCC1.Cl.[OH-:22].[K+]>>[O:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:11]=[CH:10][C:9]([C:7]([OH:8])=[O:22])=[N:14][CH:13]=2)[CH2:16][CH2:17]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 671512274-[6-(Piperidin-1-ylcarbonyl)pyridin-3-yl]morpholine

Product 1

HCID 582525805-Morpholinopicolinic acidYield 71%

Procedure

25% KOH (100 mL) was added to 4-[6-(piperidin-1-ylcarbonyl)pyridin-3-yl]morphline (18.3 g), and the mixture was refluxed and then neutralized with HCl. The solution was evaporated in vacuum, and the product was extracted with hot isopropanol to give the title compound (yield 71%, 11.5 g). +ESI MS (M+H) 209.7; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.34 (br. s., 1H), 8.03 (d, 1H), 7.65 (dd, 1H), 3.75 (br. s., 4H), 3.40 (br. s., 4H).

Workup

  1. temperaturethe mixture was refluxed
  2. customThe solution was evaporated in vacuum
  3. extractionthe product was extracted with hot isopropanol

Sources & evidence

ORD record
ord-49b8afb00ad7429ab309184c594cbb87
Source dataset
uspto-grants-2014_08
Patent number
US08802690B2

Reaction notes

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