Water → HCID 12112231, compound

HRID 1168982Notes

Reaction equation

HRID 1168982 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[O:5][CH2:6][CH2:7][CH2:8][NH:9][CH3:10].[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].[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[O:5][CH2:6][CH2:7][CH2:8][NH:9][CH3:10].[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[O:5][CH2:6][CH2:7][CH2:8][NH:9][CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 10197952HCID 10197952, compound

Product 1

HCID 12112231HCID 12112231, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3-(3-aminophenoxy)propyl)methylamine (2.77 g, 15.30 mmol) in ethanol was added galactaric acid (1.61 g, 7.65 mmol). Water 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. The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. No solids had formed. Consequently, the solution was concentrated to a residue that was vacuum dried. The solids were slurried in 2-propanol, and the 2-propanol was evaporated. The resulting solids were slurried in anhydrous ether. The product was filtered, washed with ether and vacuum dried at 40° C. to give 3.928 g (89.6%) of brown, powdery crystals, mp 160-170° C. The compound exhibits a Ki of 64 nM; the effect at muscle sites is 11 percent; and the effect at ganglia sites is 5 percent. The compound exhibits neurotransmitter release of 30 percent. The compound exhibits neurotransmitter release of 60 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
  7. temperaturewas further cooled at 5° C
  8. customNo solids had formed
  9. concentrationConsequently, the solution was concentrated to a residue that
  10. customdried
  11. customthe 2-propanol was evaporated
  12. filtrationThe product was filtered
  13. washwashed with ether and vacuum
  14. customdried at 40° C.
  15. customto give 3.928 g (89.6%) of brown, powdery crystals, mp 160-170° C

Sources & evidence

ORD record
ord-cc4b8746a5cb41f8b91522523fb43503
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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