Water → HCID 12112222, compound

HRID 2305707Notes

Reaction equation

HRID 2305707 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-2aa8c7dbd4c644759607c674dc090fb5
Source dataset
uspto-grants-2002_08
Patent number
US06441006B2

Reaction notes

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