Water → Methyl(3-(5-(phenylmethoxy)(3-pyridyloxy))propyl)amine Hemigalactarate

HRID 1168950Notes

Reaction equation

HRID 1168950 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=1.[O:21]=[C:22]([OH:34])[C@@H:23]([C@H:25]([C@H:27]([C@@H:29]([C:31]([OH:33])=[O:32])[OH:30])[OH:28])[OH:26])[OH:24].O>C(O)C>[O:21]=[C:22]([OH:34])[C@@H:23]([C@H:25]([C@H:27]([C@@H:29]([C:31]([OH:33])=[O:32])[OH:30])[OH:28])[OH:26])[OH:24].[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=1.[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9881953Methyl(3-(5-(phenylmethoxy)(3-pyridyloxy))propyl)amine

Product 1

HCID 12112224Methyl(3-(5-(phenylmethoxy)(3-pyridyloxy))propyl)amine HemigalactarateYield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl(3-(5-(phenylmethoxy)(3-pyridyloxy))propyl)amine (1.07 g, 3.929 mmol) in ethanol (15 mL) was added galactaric acid (0.413 g, 1.964 mmol). Water (1.5 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) (5 mL). The filtrate was diluted with ethanol (23 mL). The mixture was allowed to cool to ambient temperature; however, no solids precipitated. The solution was concentrated by rotary evaporation and briefly dried under high vacuum. The resulting brown solids were dissolved in a mixture of hot 2-propanol (˜15 mL) and water (0.8 mL); the dark-brown solution was allowed to cool to ambient temperature. After 30 min of precipitation, the batch was diluted with 2-propanol (30 mL) and stored at 5° C. for 16 h. The resulting solids were filtered, washed with cold 2-propanol (3×5 mL) and vacuum dried at 45° C. to give 0.967 g (65.2%) of a beige powder, mp 137-140° C. The compound exhibits a Ki of 2 nM; the effect at muscle sites is 1 percent; and the effect at ganglia sites is 3 percent. The compound exhibits neurotransmitter release of 38 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 (23 mL)
  7. customhowever, no solids precipitated
  8. concentrationThe solution was concentrated by rotary evaporation
  9. custombriefly dried under high vacuum
  10. dissolutionThe resulting brown solids were dissolved in a mixture of hot 2-propanol (˜15 mL) and water (0.8 mL)
  11. temperatureto cool to ambient temperature
  12. customAfter 30 min of precipitation
  13. additionthe batch was diluted with 2-propanol (30 mL)
  14. filtrationThe resulting solids were filtered
  15. washwashed with cold 2-propanol (3×5 mL) and vacuum
  16. customdried at 45° C.

Sources & evidence

ORD record
ord-0aadfd4b060f48729ca637f803725b1a
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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