Water → HCID 131723461, compound

HRID 1168938Notes

Reaction equation

HRID 1168938 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][CH3:14])[CH:12]=1.[O:15]=[C:16]([OH:28])[C@@H:17]([C@H:19]([C@H:21]([C@@H:23]([C:25]([OH:27])=[O:26])[OH:24])[OH:22])[OH:20])[OH:18].O>C(O)C>[O:15]=[C:16]([OH:28])[C@@H:17]([C@H:19]([C@H:21]([C@@H:23]([C:25]([OH:27])=[O:26])[OH:24])[OH:22])[OH:20])[OH:18].[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][CH3:14])[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][CH3:14])[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 10176531HCID 10176531, compound

Product 1

HCID 131723461HCID 131723461, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl(3-(5-methoxy-3-pyridyloxy)propyl)amine (0.228 g, 1.16 mmol) in ethanol (4.3 mL) was added galactaric acid (122.0 mg, 0.58 mmol). Water (1.2 mL) was added drop-wise, while warming the solution to near reflux. To remove some white, insoluble crystals, 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) (1.4 mL). The filtrate was diluted with ethanol (6.5 mL), producing a white precipitate. The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 48 h. The precipitate was filtered, washed with ethanol (10 mL), and vacuum dried at 40° C. for 24 h to give 141.2 mg (80.7%) of a white, crystalline solid, mp 140-141° C. The compound exhibits a Ki of 15 nM; the effect at muscle sites is 10 percent; and the effect at ganglia sites is 5 percent. The compound exhibits neurotransmitter release of 54 percent.

Workup

  1. temperaturewhile warming the solution
  2. temperatureto near reflux
  3. customTo remove some white, insoluble crystals
  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, v/v) (1.4 mL)
  6. additionThe filtrate was diluted with ethanol (6.5 mL)
  7. customproducing a white precipitate
  8. temperaturewas further cooled at 5° C. for 48 h
  9. filtrationThe precipitate was filtered
  10. washwashed with ethanol (10 mL), and vacuum
  11. customdried at 40° C. for 24 h
  12. customto give 141.2 mg (80.7%) of a white, crystalline solid, mp 140-141° C

Sources & evidence

ORD record
ord-28d00280893840249633eafa9d848c28
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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