Water → Dimethyl(3-(3-pyridyloxy)propyl)amine Hem igalactarate

HRID 1168919Notes

Reaction equation

HRID 1168919 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=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].[CH3:13][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9794053Dimethyl(3-(3-pyridyloxy)propyl)amine

Product 1

HCID 12112217Dimethyl(3-(3-pyridyloxy)propyl)amine Hem igalactarateYield 103%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of dimethyl(3-(3-pyridyloxy)propyl)amine (1.95 g, 10.8 mmol) in ethanol (15 mL) was added galactaric acid (0.696 g, 3.30 mmol). Water (4 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). The filtrate was diluted with ethanol (80 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 16 h. No solids precipitated. Consequently, the solution was concentrated to a crystalline solid. The solid was slurried in ether, filtered, washed with ether, and vacuum dried at 40° C. to give 1.94 g (62.7%) of brown powdery crystals, mp 137-140° C. The compound exhibits a Ki of 126 nM; the effect at muscle sites is 8 percent; and the effect at ganglia sites is 5 percent. The compound exhibits neurotransmitter release of 32 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. for 16 h
  8. customNo solids precipitated
  9. concentrationConsequently, the solution was concentrated to a crystalline solid
  10. filtrationfiltered
  11. washwashed with ether, and vacuum
  12. customdried at 40° C.

Sources & evidence

ORD record
ord-e935e51733954a07a83fa4fd55f6c1de
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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