Water → Dimethyl(4-(3-pvridyloxy)butyl)amine Hemigalactarate

HRID 2305704Notes

Reaction equation

HRID 2305704 reaction equation
[CH3:1][N:2]([CH3:14])[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:15]=[C:16]([OH:28])[C@@H:17]([C@H:19]([C@H:21]([C@@H:23]([C:25]([OH:27])=[O:26])[OH:24])[OH:22])[OH:20])[OH:18].O>C(O)C>[O:15]=[C:16]([OH:28])[C@@H:17]([C@H:19]([C@H:21]([C@@H:23]([C:25]([OH:27])=[O:26])[OH:24])[OH:22])[OH:20])[OH:18].[CH3:14][N:2]([CH3:1])[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][N: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)[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9794168Dimethyl(4-(3-pyridyloxy)butyl)amine

Product 1

HCID 131723460Dimethyl(4-(3-pvridyloxy)butyl)amine Hemigalactarate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of dimethyl(4-(3-pyridyloxy))butylamine (1.26 g, 6.49 mmol) in ethanol (10 mL) was added galactaric acid (0.682 g, 3.25 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 (80 mL). The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 16 h. Very few solids precipitated. Consequently, the solution was concentrated, and the residue was slurried in ether. The solids were filtered, washed with ether and vacuum dried at 40° C. to give 1.06 g (54.7%) of a light-brown, flaky powder, mp 127-130° C. The compound exhibits a Ki of 3410 nM. The compound exhibits neurotransmitter release of 24 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. customVery few solids precipitated
  9. concentrationConsequently, the solution was concentrated
  10. filtrationThe solids were filtered
  11. washwashed with ether and vacuum
  12. customdried at 40° C.
  13. customto give 1.06 g (54.7%) of a light-brown, flaky powder, mp 127-130° C

Sources & evidence

ORD record
ord-71dfa72abba641bcbeff9febe1715d0c
Source dataset
uspto-grants-2002_08
Patent number
US06441006B2

Reaction notes

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