Water → HCID 131723462, compound

HRID 1168956Notes

Reaction equation

HRID 1168956 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[C:8]([CH3:13])=[N:9][CH:10]=[CH:11][CH:12]=1.[O:14]=[C:15]([OH:27])[C@@H:16]([C@H:18]([C@H:20]([C@@H:22]([C:24]([OH:26])=[O:25])[OH:23])[OH:21])[OH:19])[OH:17].O>C(O)C>[O:14]=[C:15]([OH:27])[C@@H:16]([C@H:18]([C@H:20]([C@@H:22]([C:24]([OH:26])=[O:25])[OH:23])[OH:21])[OH:19])[OH:17].[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[C:8]([CH3:13])=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[C:8]([CH3:13])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 10219684HCID 10219684, compound

Product 1

HCID 131723462HCID 131723462, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl(3-(2-methyl(3-pyridyloxy))propyl)amine (1.19 g, 6.61 mmol) in ethanol (12 mL) was added galactaric acid (0.696 g, 3.30 mmol). Water (3 mL) was added drop-wise, while warming the solution to reflux. To remove some white, insoluble solids, the warm solution was filtered through a glass wool plug, washing the filter plug with a warm solution of ethanol-water (4:1, v/v) (4 mL). The filtrate was diluted with ethanol (30 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 48 h. No solids precipitated. Consequently, the solution was concentrated to a flaky solid. The solid was slurried in 2-propanol, filtered, washed with 2-propanol, and vacuum dried at 40° C. to give 1.37 g (72.8%) of an off-white, flaky powder, mp 145-148° C. The compound exhibits a Ki of 236 nM; the effect at muscle sites is 0 percent; and the effect at ganglia sites is 15 percent. The compound exhibits neurotransmitter release of 69 percent.

Workup

  1. temperaturewhile warming the solution
  2. temperatureto reflux
  3. customTo remove some white, insoluble solids
  4. filtrationthe warm solution was filtered through a glass wool plug
  5. washwashing the filter plug with a warm solution of ethanol-water (4:1
  6. additionThe filtrate was diluted with ethanol (30 mL)
  7. temperaturewas further cooled at 5° C. for 48 h
  8. customNo solids precipitated
  9. concentrationConsequently, the solution was concentrated to a flaky solid
  10. filtrationfiltered
  11. washwashed with 2-propanol, and vacuum
  12. customdried at 40° C.
  13. customto give 1.37 g (72.8%) of an off-white, flaky powder, mp 145-148° C

Sources & evidence

ORD record
ord-19490cf62e1e4c13bae1b9a8d59646fa
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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