Water → HCID 12112225, compound

HRID 1168953Notes

Reaction equation

HRID 1168953 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[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[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1.[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 10176377HCID 10176377, compound

Product 1

HCID 12112225HCID 12112225, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl(3-(6-methyl(3-pyridyloxy))propyl)amine (1.224 g, 6.80 mmol) in ethanol (15 mL) was added galactaric acid (0.714 g, 3.40 mmol). Water (4 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). The filtrate was diluted with ethanol (20 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 72 h. The resulting solids were filtered, washed with cold ethanol, and vacuum dried at 40° C. to give 1.596 g (82.3%) of a white, fluffy crystalline powder, mp 152-155° C. The compound exhibits a Ki of 12 nM; and the effect at muscle sites is 0 percent. The compound exhibits neurotransmitter release of 77 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 (20 mL)
  7. temperaturewas further cooled at 5° C. for 72 h
  8. filtrationThe resulting solids were filtered
  9. washwashed with cold ethanol, and vacuum
  10. customdried at 40° C.
  11. customto give 1.596 g (82.3%) of a white, fluffy crystalline powder, mp 152-155° C

Sources & evidence

ORD record
ord-997f6018747749cf8d793aa9ca13d3de
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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