Water → HCID 131723463, compound

HRID 2305730Notes

Reaction equation

HRID 2305730 reaction equation
[CH3:1][NH:2][CH:3]([CH3:13])[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].[CH3:1][NH:2][CH:3]([CH3:13])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:1][NH:2][CH:3]([CH3:13])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9834124HCID 9834124, compound

Product 1

HCID 131723463HCID 131723463, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl(1-methyl-3-(3-pyridyloxy)propyl)amine (0.92 g, 5.11 mmol) in ethanol (25 mL) at 70° C. was added galactaric acid (0.537 g, 2.55 mmol). Water (0.5 mL) was added drop-wise, while stirring producing a clear solution. Some white, insoluble solids were removed by filtration. The filtrate was concentrated to 15 mL, and was allowed to cool to ambient temperature. After standing for 16 h, the precipitate was filtered, washed with ether (10 mL) and vacuum dried at 45° C. for 18 h to give 1.15 g (78.9%) of an off-white, amorphous powder, mp 134-136° C. The compound exhibits a Ki of 138 nM; the effect at muscle sites is 16 percent; and the effect at ganglia sites is 20 percent. The compound exhibits neurotransmitter release of 49 percent.

Workup

  1. customproducing a clear solution
  2. customSome white, insoluble solids were removed by filtration
  3. concentrationThe filtrate was concentrated to 15 mL
  4. filtrationthe precipitate was filtered
  5. washwashed with ether (10 mL) and vacuum
  6. customdried at 45° C. for 18 h
  7. customto give 1.15 g (78.9%) of an off-white, amorphous powder, mp 134-136° C

Sources & evidence

ORD record
ord-665c36ff0df844ee8d3d97b16b231059
Source dataset
uspto-grants-2002_08
Patent number
US06441006B2

Reaction notes

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