Water → (4E)-N-Methyl-5-(5-i sopropoxy-3-pyridyl)-4-penten-2-amine Hemigalactarate

HRID 968400Notes

Reaction equation

HRID 968400 reaction equation
[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[CH:13]=1)[CH3:4].[O:18]=[C:19]([OH:31])[C@@H:20]([C@H:22]([C@H:24]([C@@H:26]([C:28]([OH:30])=[O:29])[OH:27])[OH:25])[OH:23])[OH:21].O>CO>[O:18]=[C:19]([OH:31])[C@@H:20]([C@H:22]([C@H:24]([C@@H:26]([C:28]([OH:30])=[O:29])[OH:27])[OH:25])[OH:23])[OH:21].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[CH:13]=1)[CH3:4].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[CH:13]=1)[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9881145(4E)-N-methyl-5-(5-isopropoxy-3-pyridinyl)-4-penten-2-amine

Product 1

HCID 131722558(4E)-N-Methyl-5-(5-i sopropoxy-3-pyridyl)-4-penten-2-amine HemigalactarateYield 93.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4E)-N-Methyl-5-(5-isopropoxy-3-pyridyl)4-penten-2-amine (69.3 mg, 0.23 mmol) was dissolved in CH3OH (1.5 mL), assisted by heating. The warm solution was treated with galactaric acid (24.3 mg, 0.12 mmol), followed by water (0.3 mL). The resulting solution was warmed and filtered through glass wool to remove a few insoluble particles, washing the filter plug with 0.4 mL of a CH3OH—H2O (4:1, v/v) solution. The filtrate was diluted with CH3OH (1.5 mL), and the light-yellow solution was stored at 5° C. for 15 h. No precipitate had formed; therefore, the solution was concentrated on a rotary evaporator. The resulting solids were triturated with anhydrous diethyl ether (3×6 mL). The product was dried under a stream of nitrogen, dried under high vacuum, followed by further vacuum drying at 45° C. for 15 h to afford 73.0 mg (93.1%) of an off-white powder, mp 144-146.5° C.

Workup

  1. temperatureby heating
  2. temperatureThe resulting solution was warmed
  3. filtrationfiltered through glass wool
  4. customto remove a few insoluble particles
  5. washwashing the filter plug with 0.4 mL of a CH3OH—H2O (4:1
  6. additionThe filtrate was diluted with CH3OH (1.5 mL)
  7. customNo precipitate had formed
  8. concentrationtherefore, the solution was concentrated on a rotary evaporator
  9. customThe resulting solids were triturated with anhydrous diethyl ether (3×6 mL)
  10. customThe product was dried under a stream of nitrogen
  11. customdried under high vacuum
  12. customdrying at 45° C. for 15 h

Sources & evidence

ORD record
ord-6c4be9f3bb9c464bb02a447bd0e55836
Source dataset
uspto-grants-2005_10
Patent number
US06958399B2

Reaction notes

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