Water → HCID 12112222, compound

HRID 1168933Notes

Reaction equation

HRID 1168933 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][NH:12][CH3:13])[CH:5]=[N:6][CH:7]=1.[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].[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][NH:12][CH3:13])[CH:5]=[N:6][CH:7]=1.[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][NH:12][CH3:13])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9859051HCID 9859051, compound

Product 1

HCID 12112222HCID 12112222, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3-(5-chloro(3-pyridyloxy))propyl)methylamine (1.00 g, 5.00 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. The solids were filtered, washed and vacuum dried at 40° C. to give 1.163 g (76.3%) of off-white, powdery crystals, mp 173-174° C. The compound exhibits a Ki of 11 nM; the effect at muscle sites is 16 percent; and the effect at ganglia sites is 7 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. filtrationThe solids were filtered
  9. washwashed
  10. customvacuum dried at 40° C.
  11. customto give 1.163 g (76.3%) of off-white, powdery crystals, mp 173-174° C

Sources & evidence

ORD record
ord-34c40cd779f04f02bb9ef58cab877cbe
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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