Water → Methyl(4-(3-pyridyloxy)butyl)amine Hemigalactarate

HRID 1168925Notes

Reaction equation

HRID 1168925 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=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].[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9794054Methyl(4-(3-pyridyloxy)butyl)amine

Product 1

HCID 12112220Methyl(4-(3-pyridyloxy)butyl)amine Hemigalactarate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl(4-(3-pyridyloxy)butyl)amine (1.25 g, 7.50 mmol) in ethanol (15 mL) was added galactaric acid (0.858 g, 4.08 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) (4 mL). The filtrate was diluted with ethanol (40 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 16 h. The solids were filtered, washed with cold ethanol and vacuum dried at 40° C. to give 1.69 g (72.8%) of a fine, white, crystalline powder, mp 173-175° C. The compound exhibits a Ki of 5523 nM. The compound exhibits neurotransmitter release of 56 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 (40 mL)
  7. temperaturewas further cooled at 5° C. for 16 h
  8. filtrationThe solids were filtered
  9. washwashed with cold ethanol and vacuum
  10. customdried at 40° C.
  11. customto give 1.69 g (72.8%) of a fine, white, crystalline powder, mp 173-175° C

Sources & evidence

ORD record
ord-2f51b84caf324204a8db4b796ccfa3b0
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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