Water → HCID 131723090, compound

HRID 1250264Notes

Reaction equation

HRID 1250264 reaction equation
[O:1]=[C:2]([OH:14])[C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([C:11]([OH:13])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4].O.[CH3:16][NH:17][CH:18]([CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:31])[CH3:30])[CH:24]=1)[CH3:19]>CO>[O:1]=[C:2]([OH:14])[C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([C:11]([OH:13])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH3:16][NH:17][CH:18]([CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:31])[CH3:30])[CH:24]=1)[CH3:19].[CH3:16][NH:17][CH:18]([CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:31])[CH3:30])[CH:24]=1)[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 10220061HCID 10220061, compound

Product 1

HCID 131723090HCID 131723090, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In succession, galactaric acid (95 mg, 0.45 mmol) and water (0.5 mL) were added to a solution of (4E)-N-methyl-5-(3-(dimethylamino)phenyl)-4-penten-2-amine (198 mg, 0.907 mmol) in methanol (4 mL). The mixture was warmed to 60° C. and filtered through a glass wool plug. The filtrate was diluted with ethanol (4 mL) and kept at −4° C. for 16 h. Filtration and vacuum drying at 40° C., gave 218 mg (74.9% yield) of white powder, mp 164-166° C.

Workup

  1. filtrationfiltered through a glass wool plug
  2. additionThe filtrate was diluted with ethanol (4 mL)
  3. filtrationFiltration and vacuum
  4. customdrying at 40° C.

Sources & evidence

ORD record
ord-26fb7e53ce734cddbcaa3515c9500ba3
Source dataset
uspto-grants-2002_01
Patent number
US06337351B1

Reaction notes

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