Water → HCID 131723087, compound

HRID 1250254Notes

Reaction equation

HRID 1250254 reaction equation
[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)[CH3:4].[O:16]=[C:17]([OH:29])[C@@H:18]([C@H:20]([C@H:22]([C@@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23])[OH:21])[OH:19].O>C(O)C>[O:16]=[C:17]([OH:29])[C@@H:18]([C@H:20]([C@H:22]([C@@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23])[OH:21])[OH:19].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)[CH3:4].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9816269HCID 9816269, compound

Product 1

HCID 131723087HCID 131723087, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4E)-N-methyl-5-(3,4-dichlorophenyl)-4-penten-2-amine (417.7 mg, 1.711 mmol) in absolute ethanol (6.3 mL) was added galactaric acid (179.8 mg, 0.855 mmol). Water (1.3 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) (2 mL). The filtrate was diluted with ethanol (10 mL), cooled to ambient temperature, and further cooled at 5° C. for 18 h. Because only a small amount of salt precipitated, the mixture was concentrated on a rotary evaporator. The resulting off-white solids were recrystallized from 2-propanol-water. After cooling at 5° C. for 16 h, the solids were filtered, washed with cold 2-propanol and vacuum dried at 40° C. to give 407 mg (68.1%) of a white to off-white, crystalline powder, mp 155-157° 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 (10 mL)
  6. temperaturefurther cooled at 5° C. for 18 h
  7. customBecause only a small amount of salt precipitated
  8. concentrationthe mixture was concentrated on a rotary evaporator
  9. customThe resulting off-white solids were recrystallized from 2-propanol-water
  10. temperatureAfter cooling at 5° C. for 16 h
  11. filtrationthe solids were filtered
  12. washwashed with cold 2-propanol and vacuum
  13. customdried at 40° C.
  14. customto give 407 mg (68.1%) of a white to off-white, crystalline powder, mp 155-157° C.

Sources & evidence

ORD record
ord-15ca4e5a23bf4029a48290abb18416d4
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

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