Water → 4-(3-Pyridyloxy)butylamine Hemigalactarate

HRID 1168922Notes

Reaction equation

HRID 1168922 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH:2]=1.[O:13]=[C:14]([OH:26])[C@@H:15]([C@H:17]([C@H:19]([C@@H:21]([C:23]([OH:25])=[O:24])[OH:22])[OH:20])[OH:18])[OH:16].O>C(O)C>[O:13]=[C:14]([OH:26])[C@@H:15]([C@H:17]([C@H:19]([C@@H:21]([C:23]([OH:25])=[O:24])[OH:22])[OH:20])[OH:18])[OH:16].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH:2]=1.[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 121122194-(Pyridin-3-yloxy)butan-1-amine

Product 1

HCID 121122184-(3-Pyridyloxy)butylamine Hemigalactarate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(3-pyridyloxy)butylamine (1.25 g, 7.50 mmol) in ethanol (12 mL) was added galactaric acid (0.791 g, 3.76 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. Very few solids precipitated. Consequently, the solution was concentrated to a flaky solid. The product was slurried in 2-propanol, and the 2-propanol was decanted. The product was vacuum dried at 40° C. to give 1.28 g (62.7%) of fine, white powder, mp 177-180° C. The compound exhibits a Ki of 232 nM; the effect at muscle sites is 0 percent; and the effect at ganglia sites is 11 percent. The compound exhibits neurotransmitter release of 100 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. customVery few solids precipitated
  9. concentrationConsequently, the solution was concentrated to a flaky solid
  10. customthe 2-propanol was decanted
  11. customdried at 40° C.
  12. customto give 1.28 g (62.7%) of fine, white powder, mp 177-180° C

Sources & evidence

ORD record
ord-09684964dc364937911aa3687b994d96
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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