Water → 3-(3-Pyridyloxy)propylamine Hemigalactarate

HRID 1168916Notes

Reaction equation

HRID 1168916 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:2]=1.[O:12]=[C:13]([OH:25])[C@@H:14]([C@H:16]([C@H:18]([C@@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19])[OH:17])[OH:15].O>C(O)C>[O:12]=[C:13]([OH:25])[C@@H:14]([C@H:16]([C@H:18]([C@@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19])[OH:17])[OH:15].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:2]=1.[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 102195403-(3-Pyridyloxy)propylamine

Product 1

HCID 1317234593-(3-Pyridyloxy)propylamine HemigalactarateYield 58.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(3-pyridyloxy)propylamine (0.354 g, 2.30.mmol) in ethanol (5 mL) was added galactaric acid (0.244 g, 1.16 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). The filtrate was diluted with ethanol (25 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 16 h. The solids were filtered, washed with cold ethanol (5 mL), and vacuum dried at 40° C. to give 344.8 mg (58.3%) of light-yellow crystals, mp 176-178° C. The compound exhibits a Ki of 65 nM; the effect at muscle sites is 0 percent; and the effect at ganglia sites is 0 percent. The compound exhibits a Ki of 12 nM; the effect at muscle sites is 0 percent; and the effect at ganglia sites is 0 percent. The compound exhibits neurotransmitter release of 0 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 (25 mL)
  7. temperaturewas further cooled at 5° C. for 16 h
  8. filtrationThe solids were filtered
  9. washwashed with cold ethanol (5 mL), and vacuum
  10. customdried at 40° C.

Sources & evidence

ORD record
ord-2cb7d886a07b4b9d818d09d019f52f06
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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