Water → HCID 131723088, compound

HRID 1250257Notes

Reaction equation

HRID 1250257 reaction equation
[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1)[CH3:4].[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].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1)[CH3:4].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 10219784HCID 10219784, compound

Product 1

HCID 131723088HCID 131723088, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4E)-N-methyl-5-(3-fluorophenyl)-4-penten-2-amine (228.5 mg, 1.182 mmol) in absolute ethanol (3.6 mL) was added galactaric acid (124.2 mg, 0.591 mmol). Water (0.7 mL) was added drop-wise while gently warming the solution. The solution was filtered through glass wool to remove a few insoluble particles, washing the filter plug with ethanol-water (4:1, v/v) (1 mL). The filtrate was diluted with ethanol (5.6 mL), cooled to ambient temperature, and further cooled at 5° C. for 18 h. The solids were filtered, washed with cold ethanol and vacuum dried at 40° C. to give 246 mg (69.6%) of a fluffy white, crystalline powder, mp 164-166° C.

Workup

  1. temperaturewhile gently warming the solution
  2. filtrationThe solution was filtered through glass wool
  3. customto remove a few insoluble particles
  4. washwashing the filter plug with ethanol-water (4:1
  5. additionThe filtrate was diluted with ethanol (5.6 mL)
  6. temperaturefurther cooled at 5° C. for 18 h
  7. filtrationThe solids were filtered
  8. washwashed with cold ethanol and vacuum
  9. customdried at 40° C.
  10. customto give 246 mg (69.6%) of a fluffy white, crystalline powder, mp 164-166° C.

Sources & evidence

ORD record
ord-73c38fa8f81e4966a7812f2e926a6c2d
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

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