Water → HCID 12112230, compound

HRID 2305734Notes

Reaction equation

HRID 2305734 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1.[O:16]=[C:17]([OH:29])[C@@H:18]([C@H:20]([C@H:22]([C@@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23])[OH:21])[OH:19].O>C(O)C>[O:16]=[C:17]([OH:29])[C@@H:18]([C@H:20]([C@H:22]([C@@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23])[OH:21])[OH:19].[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1.[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 10176686HCID 10176686, compound

Product 1

HCID 12112230HCID 12112230, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl(3-(3-nitrophenoxy)propyl)amine (493 mg, 2.35 mmol) in ethanol (10 mL) was added galactaric acid (247 mg, 1.17 mmol). Water (3.0 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). The filtrate was diluted with ethanol (15 mL), producing a white precipitate. The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. The precipitate was filtered, washed with ethanol (10 mL), and vacuum dried at 40° C. for 24 h to give 617 mg (83.5%) of white, fluffy, crystals, mp 186-187° C. The compound exhibits a Ki of 392 nM; the effect at muscle sites is 10 percent; and the effect at ganglia sites is 9 percent. The compound exhibits neurotransmitter release of 67 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)
  6. additionThe filtrate was diluted with ethanol (15 mL)
  7. customproducing a white precipitate
  8. temperaturewas further cooled at 5° C
  9. filtrationThe precipitate was filtered
  10. washwashed with ethanol (10 mL), and vacuum
  11. customdried at 40° C. for 24 h
  12. customto give 617 mg (83.5%) of white, fluffy, crystals, mp 186-187° C

Sources & evidence

ORD record
ord-9dd1c9fd95cc47228d8aa3e5e2670569
Source dataset
uspto-grants-2002_08
Patent number
US06441006B2

Reaction notes

Loading…