Water → HCID 131723465, compound

HRID 2305737Notes

Reaction equation

HRID 2305737 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=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].[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=1.[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 22989726HCID 22989726, compound

Product 1

HCID 131723465HCID 131723465, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(3-aminopropoxy)phenylamine (1.37 g, 8.25 mmol) in ethanol (12 mL) was added galactaric acid (0.867 g, 4.13 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 (80 mL). 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 hot 2-propanol and cooled to ambient temperature. The product was filtered, washed with 2-propanol and vacuum dried at 40° C. to give 1.462 g (65.4%) of a beige, crystalline powder, mp 182-185° C. The compound exhibits a Ki of 442 nM. The compound exhibits neurotransmitter release of 14 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 (80 mL)
  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. temperaturecooled to ambient temperature
  12. filtrationThe product was filtered
  13. washwashed with 2-propanol and vacuum
  14. customdried at 40° C.
  15. customto give 1.462 g (65.4%) of a beige, crystalline powder, mp 182-185° C

Sources & evidence

ORD record
ord-ab7abf8a626c481282c019d77359b9f0
Source dataset
uspto-grants-2002_08
Patent number
US06441006B2

Reaction notes

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