Water → HCID 131723463, compound

HRID 1168969Notes

Reaction equation

HRID 1168969 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-eb2e2eab4a164813af1bca2836b872b1
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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