Water → HCID 131723086, compound

HRID 1250251Notes

Reaction equation

HRID 1250251 reaction equation
[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[CH:9]=1)[CH3:4].[O:17]=[C:18]([OH:30])[C@@H:19]([C@H:21]([C@H:23]([C@@H:25]([C:27]([OH:29])=[O:28])[OH:26])[OH:24])[OH:22])[OH:20].O>C(O)C>[O:17]=[C:18]([OH:30])[C@@H:19]([C@H:21]([C@H:23]([C@@H:25]([C:27]([OH:29])=[O:28])[OH:26])[OH:24])[OH:22])[OH:20].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[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]2[O:14][CH2:15][O:16][C:10]=2[CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 10198334HCID 10198334, compound

Product 1

HCID 131723086HCID 131723086, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4E)-N-methyl-5-(3,4-methylenedioxyphenyl)-4-penten-2-amine (228.7 mg, 1.043 mmol) in absolute ethanol (3.5 mL) was added galactaric acid (109.6 mg, 0.522 mmol). Water (1.2 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 (7 mL), cooled to ambient temperature, and further cooled at 5° C. for 18 h. The product was filtered, washed with cold ethanol, and vacuum dried at 40° C. to afford 292 mg (86.2%) of a white, crystalline powder, mp 172-176° 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 (7 mL)
  6. temperaturefurther cooled at 5° C. for 18 h
  7. filtrationThe product was filtered
  8. washwashed with cold ethanol, and vacuum
  9. customdried at 40° C.
  10. customto afford 292 mg (86.2%) of a white, crystalline powder, mp 172-176° C.

Sources & evidence

ORD record
ord-34bbdb1b47274e78b44582ead604c10d
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

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