Water → (3-(3-Pyridyloxy)propyl)methylamine Hemigalactarate

HRID 2305688Notes

Reaction equation

HRID 2305688 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][CH2:10][NH:11][CH3:12])[CH:2]=1.[O:13]=[C:14]([OH:26])[C@@H:15]([C@H:17]([C@H:19]([C@@H:21]([C:23]([OH:25])=[O:24])[OH:22])[OH:20])[OH:18])[OH:16].O>C(O)C>[O:13]=[C:14]([OH:26])[C@@H:15]([C@H:17]([C@H:19]([C@@H:21]([C:23]([OH:25])=[O:24])[OH:22])[OH:20])[OH:18])[OH:16].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][CH2:10][NH:11][CH3:12])[CH:2]=1.[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][CH2:10][NH:11][CH3:12])[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9793927(3-(3-Pyridyloxy)propyl)methylamine

Product 1

HCID 131722238(3-(3-Pyridyloxy)propyl)methylamine Hemigalactarate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3-(3-pyridyloxy)propyl)methylamine (800.0 mg, 4.81 mmol) in ethanol (12 mL) was added galactaric acid (505.7 mg, 2.41 mmol). Water (2.5 mL) was added dropwise, while gently warming the light-yellow solution. 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 (18 mL), producing a white precipitate. The mixture was allowed to cool to ambient temperature and was further cooled at 5° C. for 15 h. The precipitate was filtered, washed with ethanol (6 mL), vacuum dried at 45° C. for 10 h, followed by further vacuum drying at ambient temperature for 48 h to give 994.4 mg (76.1%) of an off-white, crystalline powder, mp 161-165.5° C.

Workup

  1. temperaturewhile gently warming the light-yellow solution
  2. customTo remove some white, insoluble solids
  3. filtrationthe warm solution was filtered through a glass wool plug
  4. washwashing the filter plug with a warm solution of ethanol-water (4:1
  5. additionThe filtrate was diluted with ethanol (18 mL)
  6. customproducing a white precipitate
  7. temperaturewas further cooled at 5° C. for 15 h
  8. filtrationThe precipitate was filtered
  9. washwashed with ethanol (6 mL), vacuum
  10. customdried at 45° C. for 10 h
  11. customdrying at ambient temperature for 48 h
  12. customto give 994.4 mg (76.1%) of an off-white, crystalline powder, mp 161-165.5° C.

Sources & evidence

ORD record
ord-ae9f993cedb14a519664534d5ad8600a
Source dataset
uspto-grants-2002_08
Patent number
US06441006B2

Reaction notes

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